Cationic monobenzenic dyes, their use for the oxidation-dyeing of keratin fibers, dye compositions and dyeing processes

ABSTRACT

The invention relates to novel monobenzenic dyes including at least one cationic group Z, Z chosen from quaternized aliphatic chains, aliphatic chains including at least one quaternized saturated ring and aliphatic chains including at least one quaternized unsaturated ring, to their use as oxidation-dye precursors for the oxidation-dyeing of keratin fibers, to dye compositions containing them and to oxidation-dyeing processes using them.

The invention relates to novel monobenzenic dyes comprising at least onecationic group Z, Z chosen from quaternized aliphatic chains, aliphaticchains comprising at least one quaternized saturated ring and aliphaticchains comprising at least one quaternized unsaturated ring, to theiruse as oxidation-dye precursors for the oxidation-dyeing of keratinfibers, to dye compositions containing them and to oxidation-dyeingprocesses using them.

It is a known practice to dye keratin fibers, in particular human hair,with dye compositions comprising oxidation-dye precursors, in particularpara-phenylenediamines, ortho-aminophenols or para-aminophenols andheterocyclic compounds such as diaminopyrazole derivatives, which aregenerally referred to as oxidation bases. The oxidation-dye precursors,or oxidation bases, are colorless or weakly coloured compounds which,when combined with oxidizing products, can give rise to colouredcompounds and dyes by a process of oxidative condensation.

It is also known that the shades obtained with these oxidation bases canbe varied by combining them with couplers or coloration modifiers, thelatter being chosen in particular from aromatic meta-diamines,meta-aminophenols, meta-diphenols and certain heterocyclic compoundssuch as, for example, indole couplers.

The variety of molecules used as oxidation bases and couplers makes itpossible to obtain a wide range of colors. The so-called “permanent”coloration obtained by means of these oxidation dyes must, moreover,satisfy a certain number of requirements. Specifically, the oxidationdyes must have no toxicological drawbacks, must allow shades of thedesired strength to be obtained, and have good resistance to externalagents (light, bad weather, washing, permanent-waving, perspiration andfriction).

The dyes must also allow white hairs to be covered. Lastly, they must beas unselective as possible, i.e., they must allow the smallest possibledifferences in coloration to be produced over the entire length of thesame keratin fiber, which may indeed be differently sensitized (i.e.,damaged) between its tip and its root.

The inventors have discovered, entirely surprisingly and unexpectedly,that novel cationic monobenzenic dyes of formula (I) defined below,comprising at least one cationic group Z, Z chosen from quaternizedaliphatic chains, aliphatic chains comprising at least one quaternizedsaturated ring and aliphatic chains comprising at least one quaternizedunsaturated ring, are not only suitable for use as oxidation-dyeprecursors, but also allow dye compositions to be obtained which lead tostrong colorations, in a wide range of shades, and which have excellentproperties of resistance to the various treatments to which keratinfibers may be subjected.

These discoveries form the basis of the present invention.

A first subject of the invention is thus novel compounds of formula (I)below, and the acid addition salts thereof:

in which:

A₁, A₂ and A₃, which may be identical or different, are chosen from agroup —NR₇R₈ and a hydroxyl radical; one and only one of the groups A₁,A₂ and A₃ can also represent a group R₃ as defined below;

R₁, R₂ and R₃, which may be identical or different, are chosen from ahydrogen atom; a halogen atom; a group Z as defined below; a

(C₁-C₆)alkylcarbonyl radical; an amino(C₁-C₆)alkylcarbonyl radical; anN-Z-amino(C₁-C₆)alkylcarbonyl radical; anN-(C₁-C₆)alkylamino(C₁-C₆)alkylcarbonyl radical; anN,N-di(C₁-C₆)alkylamino (C₁-C₆)alkylcarbonyl radical; anamino(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radical; an

N-Z-amino(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radical; anN-(C₁-C₆)alkylamino(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radical; anN,N-di(C₁-C₆) alkylamino(C₁-C₆) alkylcarbonyl(C₁-C₆)alkyl radical; acarboxyl radical; a (C₁-C₆)alkylcarboxyl radical; a(C₁-C₆)alkylsulphonyl radical; an aminosulphonyl radical; an

N-Z-aminosulphonyl radical; a (C₁-C₆)N-alkylaminosulphonyl radical; an

N,N-di(C₁-C₆)alkylaminosulphonyl radical; a (C₁-C₆)aminosulphonylalkylradical; a (C₁-C₆)N-Z-aminosulphonylalkyl radical; an

N-(C₁-C₆)alkylaminosulphonyl(C₁-C₆)alkyl radical; an

N,N-di(C₁-C₆)alkylaminosulphonyl(C₁-C₆)alkyl radical; a carbamylradical; an

N-(C₁-C₆)alkylcarbamyl radical; an N,N-di(C₁-C₆)alkylcarbamyl radical; a

carbamyl(C₁-C₆)alkyl radical; an N-(C₁-C₆)alkylcarbamyl(C₁-C₆)alkylradical;

an N,N-di(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radical; a (C₁-C₆)alkylradical; a

(C₁-C₆)monohydroxyalkyl radical; a (C₂-C₆)polyhydroxyalkyl radical; a(C₁-C₆)alkoxy(C₁-C₆)alkyl radical; a (C₁-C₆)trifluoroalkyl radical; acyano radical; a group OR₆ or SR₆; an amino group protected by a(C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylcarboxyl,trifluoro(C₁-C₆)alkylcarbonyl, amino(C₁-C₆)alkylcarbonyl,N-Z-amino(C₁-C₆)alkylcarbonyl, N-(C₁-C₆)alkylamino(C₁-C₆)alkylcarbonyl,N,N-di(C₁-C₆)alkylamino(C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylcarboxyl,carbamyl, N-(C₁-C₆)alkylcarbamyl, N,N-di(C₁-C₆)alkylcarbamyl, C₁-C₆alkylsulphonyl, aminosulphonyl, N-Z-aminosulphonyl,(C₁-C₆)N-alkylaminosulphonyl, N,N-di(C₁-C₆)alkylaminosulphonyl,thiocarbamyl or formyl radical, or with the group Z defined below inwhich a linker arm D comprises a ketone function directly attached tothe nitrogen atom of the amino group; a

(C₁-C₆)aminoalkyl radical in which the alkyl is unsubstituted orsubstituted with one or more hydroxyl radicals; a (C₁-C₆)aminoalkylradical in which the alkyl is unsubstituted or substituted with one ormore hydroxyl radicals and in which the amine is substituted with one ortwo radicals, which may be identical or different, chosen from alkyl,(C₁-C₆)monohydroxyalkyl, (C₂-C₆)polyhydroxyalkyl, (C₁-C₆)alkylcarbonyl,carbamyl, N-(C₁-C₆)alkylcarbamyl, N,N-di(C₁-C₆)alkylcarbamyl,(C₁-C₆)alkylsulphonyl, formyl, trifluoro(C₁-C₆)alkylcarbonyl,(C₁-C₆)alkylcarboxyl and thiocarbamyl radicals, or from a group Z asdefined below, or which may form, together with the nitrogen atom towhich they are attached, a carbonaceous 5- or 6-membered ring or whichcontains one or more hetero atoms;

R₆ is chosen from a (C₁-C₆)alkyl radical; a (C₁-C₆)monohydroxyalkylradical; a

(C₂-C₆)polyhydroxyalkyl radical; a group Z as defined below; a

(C₁-C₆)alkoxy(C₁-C₆)alkyl radical; an aryl radical; a benzyl radical; a

carboxy(C₁-C₆)alkyl radical; a (C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radical;a cyano(C₁-C₆)alkyl radical; a carbamyl(C₁-C₆)alkyl radical; anN-(C₁-C₆)alkyl carbamyl(C₁-C₆)alkyl radical; anN,N-di(C₁-C₆)alkylcarbamyl (C₁-C₆)alkyl

radical; a (C₁-C₆)trifluoroalkyl radical; a (C₁-C₆)aminosulphonylalkylradical; a

(C₁-C₆)N-Z-aminosulphonylalkyl radical; an N-(C₁-C₆)alkylamino-sulphonyl(C₁-C₆)alkyl radical; anN,N-di(C₁-C₆)alkylaminosulphonyl-(C₁-C₆)alkyl radical; a(C₁-C₆)alkylsulphinyl (C₁-C₆)alkyl radical; a

(C₁-C₆)alkylsulphonyl (C₁-C₆)alkyl radical; a (C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radical; a (C₁-C₆)aminoalkyl radical in which the alkyl isunsubstituted or substituted with one or more hydroxyl radicals; a(C₁-C₆)aminoalkyl radical in which the alkyl is unsubstituted orsubstituted with one or more hydroxyl radicals and in which the amine issubstituted with one or two identical or different radicals chosen from(C₁-C₆)alkyl, (C₁-C₆)monohydroxyalkyl, (C₂-C₆)polyhydroxyalkyl,(C₁-C₆)alkylcarbonyl, formyl, trifluoro-(C₁-C₆)alkylcarbonyl,(C₁-C₆)alkylcarboxyl, carbamyl, N-(C₁-C₆)alkylcarbamyl,N,N-di-(C₁-C₆)alkylcarbamyl, thiocarbamyl and (C₁-C₆) alkylsulphonylradicals, or from a group Z as defined below; or which may form,together with the nitrogen atom to which they are attached, acarbonaceous 5- or 6-membered ring or which contains one or more heteroatoms;

R₄, R₅, R₇ and R₈, which may be identical or different, are chosen froma hydrogen atom; a group Z as defined below, in which the linker arm Dcontains no ketone functions directly linked to the nitrogen atomcarrying the R₄ and R₅ radicals; a (C₁-C₆)alkyl radical; a (C₁-C₆)monohydroxyalkyl radical;

a (C₂-C₆)polyhydroxyalkyl radical; a (C₁-C₆)alkoxy(C₁-C₆)alkyl radical;an aryl radical; a benzyl radical; a cyano(C₁-C₆)alkyl radical; acarbamyl(C₁-C₆)alkyl radical; an N-(C₁-C₆)alkylcarbamyl(C₁-C₆)alkylradical; an

N,N-di(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radical; athiocarbamyl(C₁-C₆)alkyl radical; a (C₁-C₆)trifluoroalkyl radical; a(C₁-C₆)sulphoalkyl radical; a

(C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radical; a(C₁-C₆)alkylsulphinyl(C₁-C₆)alkyl radical; a (C₁-C₆)aminosulphonylalkylradical; a

(C₁-C₆)N-Z-aminosulphonylalkyl radical; an

N-(C₁-C₆)alkylaminosulphonyl(C₁-C₆)alkyl radical; an

N,N-di(C₁-C₆)alkylaminosulphonyl(C₁-C₆)alkyl radical; a

(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radical; a (C₁-C₆)aminoalkyl radical inwhich the alkyl is unsubstituted or substituted with one or morehydroxyl radicals; a

(C₁-C₆)aminoalkyl radical in which the alkyl is unsubstituted orsubstituted with one or more hydroxyl radicals and in which the amine issubstituted with one or two identical or different radicals chosen from(C₁-C₆)alkyl, (C₁-C₆)monohydroxyalkyl, (C₂-C₆)polyhydroxyalkyl,(C₁-C₆)alkylcarbonyl, carbamyl, N-(C₁-C₆)alkylcarbamyl,N,N-di(C₁-C₆)alkylcarbamyl, (C₁-C₆)alkylsulphonyl, formyl,trifluoro(C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylcarboxyl and thiocarbamylradicals, or from a group Z as defined below; or which may form,together with the nitrogen atom to which they are attached, acarbonaceous 5- or 6-membered ring or which contains one or more heteroatoms;

Z is chosen from the unsaturated cationic groups of formulae (II) and(III) below, and the saturated cationic groups of formula (IV) below:

in which:

D is a linker arm which represents a linear or branched alkyl chainpreferably comprising from 1 to 14 carbon atoms, which can beinterrupted by one or more hetero atoms such as oxygen, sulphur ornitrogen atoms, and which can be substituted with one or more hydroxylor (C₁-C₆)alkoxy radicals, and which can bear one or more ketonefunctional groups;

the ring members E, G, J, L and M, which may be identical or different,are

chosen from a carbon, oxygen, sulphur or nitrogen atom;

n is an integer ranging from 0 to 4;

m is an integer ranging from 0 to 5;

the R radicals, which may be identical or different, are chosen from asecond

group Z identical to or different from the first group Z; a halogenatom; a

hydroxyl radical; a (C₁-C₆)alkyl radical; a (C₁-C₆)monohydroxyalkylradical; a

(C₂-C₆)polyhydroxyalkyl radical; a nitro radical; a cyano radical; a

cyano(C₁-C₆)alkyl radical; a C₁-C₆ alkoxy radical; a

tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radical; an amido radical; an aldehydoradical; a carboxyl radical; a (C₁-C₆)alkylcarbonyl radical; a thioradical; a

(C₁-C₆)thioalkyl radical; a (C₁-C₆)alkylthio radical; an amino radical;an amino radical protected with a (C₁-C₆)alkylcarbonyl; carbamyl or(C₁-C₆)alkylsulphonyl radical; or an NHRO or NROR″ group in which RO andR″, which may be identical or different, are chosen from a (C₁-C₆)alkylradical, a (C₁-C₆)monohydroxyalkyl radical or a (C₂-C₆)polyhydroxyalkylradical;

R₉ is chosen from a (C₁-C₆)alkyl radical; a (C₁-C₆)monohydroxyalkylradical; a

(C₂-C₆)polyhydroxyalkyl radical; a cyano(C₁-C₆)alkyl radical; a

tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radical; a (C₁-C₆)alkoxy(C₁-C₆)alkylradical; a

carbamyl-(C₁-C₆)alkyl radical; a (C₁-C₆)alkylcarboxy(C₁-C₆)-alkylradical; a benzyl radical or a second group Z identical to or differentfrom the first group Z;

R₁₀, R₁₁ and R₁₂, which may be identical or different, are chosen from a(C₁-C₆)alkyl radical; a (C₁-C₆)monohydroxyalkyl radical; a

(C₂-C₆)polyhydroxyalkyl radical; a (C₁-C₆)alkoxy(C₁-C₆)alkyl radical; a

cyano(C₁-C₆)alkyl radical; an aryl radical; a benzyl radical; a

(C₁-C₆)amidoalkyl radical; a tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicalor a (C₁-C₆)aminoalkyl radical in which the amine is protected with a(C₁-C₆)alkylcarbonyl, carbamyl or C₁-C₆ alkylsulphonyl radical; two ofthe radicals R₁₀, R₁₁ and R₁₂ may also form together, with the nitrogenatom to which they are attached, a saturated carbonaceous 5- or6-membered ring or a saturated 5- or 6-membered ring which contains oneor more heteroatoms, such as, for example, a pyrrolidine ring, apiperidine ring, a piperazine ring or a morpholine ring, it beingpossible for the ring to be unsubstituted or substituted with a halogenatom, a hydroxyl radical, a (C₁-C₆)alkyl radical, a(C₁-C₆)monohydroxyalkyl radical, a (C₂-C₆)polyhydroxyalkyl radical, anitro radical, a cyano radical, a cyano(C₁-C₆)alkyl radical, a(C₁-C₆)alkoxy radical, a tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radical, anamido radical, a formyl radical, a carboxyl radical, a keto(C₁-C₆)alkylradical, a thio radical, a (C₁-C₆)thioalkyl radical, a (C₁-C₆)alkylthioradical, an amino radical or an amino radical protected by a(C₁-C₆)alkylcarbonyl, carbamyl or (C₁-C₆)alkylsulphonyl radical;one ofthe R₁₀, R₁₁ and R₁₂ radicals can also represent a second group Zidentical to or different from the first group Z;

R₁₃ is chosen from a (C₁-C₆)alkyl radical; a (C₁-C₆)monohydroxy-alkylradical;

a (C₂-C₆)polyhydroxyalkyl radical; an aryl radical; a benzyl radical; an

amino(C₁-C₆)alkyl radical, an amino(C₁-C₆)alkyl radical, the amine ofwhich is protected by a (C₁-C₆)alkylcarbonyl, carbamyl or(C₁-C₆)alkylsulphonyl radical; a carboxy(C₁-C₆)alkyl radical; acyano(C₁-C₆)alkyl radical; a

carbamyl(C₁-C₆)alkyl radical; a trifluoro(C₁-C₆)alkyl radical; a

tri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl radical; a sulphonamido(C₁-C₆)alkylradical; a

(C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radical; a(C₁-C₆)alkylsulphinyl(C₁-C₆)alkyl radical; a(C₁-C₆)alkylsulphonyl(C₁-C₆)alkyl radical; a

(C₁-C₆)alkylketo(C₁-C₆)alkyl radical; anN-(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radical; anN-(C₁-C₆)alkylsulphonamido(C₁-C₆)alkyl radical;

a and y are integers equal to 0 or 1; with the following conditions:

in the unsaturated cationic groups of formula (II):

when a=0, the linker arm D is attached to the nitrogen atom,

when a=1, the linker arm D is attached to one of the ring members E, G,J or L,

y can take the value 1 only:

1) when the ring members E, G, J and L simultaneously represent a carbonatom and when the R₉ radical is carried by the nitrogen atom of theunsaturated ring; or else

2) when at least one of the ring members E, G, J and L represents anitrogen atom to which the R₉ radical is attached;

in the unsaturated cationic groups of formula (III):

when a=0, the linker arm D is attached to the nitrogen atom,

when a=1, the linker arm D is attached to one of the ring members E, G,J, L or M,

y can take the value 1 only when at least one of the ring members E, G,J, L and M represents a divalent atom and when the R₉ radical is carriedby the nitrogen atom of the unsaturated ring;

in the cationic groups of formula (IV):

when a=0, then the linker arm D is attached to the nitrogen atomcarrying the R₁₀ to R₁₂ radicals,

when a=1, then two of the R₁₀ to R₁₂ radicals jointly form, with thenitrogen atom to which they are attached, a saturated 5- or 6-memberedring as defined above, and the linker arm D is carried by a carbon atomof the saturated ring;

X⁻ is a monovalent or divalent anion and is preferably chosen from ahalogen atom, such as chlorine, bromine, fluorine or iodine, ahydroxide, a hydrogen sulphate or a (C₁-C₆)alkyl sulphate, such as, forexample, a methyl sulphate or an ethyl sulphate;

with the overall proviso that the number of Z cationic groups is atleast equal to 1.

As mentioned above, the colorations obtained with the oxidation-dyecomposition containing the dye(s) of formula (I) in accordance with theinvention are strong and produce a wide range of colors. They moreoverhave excellent properties of resistance to the action of variousexternal agents (light, bad weather, washing, permanent-waving,perspiration, friction). These properties are particularly noteworthywith regard to the resistance of the colorations obtained to the actionof light, washing, permanent-waving and perspiration.

In formulae (I), (II), (III) and(IV) above, the alkyl and alkoxyradicals can be linear or branched.

Examples of rings of the unsaturated Z groups of formula (II) above mayinclude, but are not limited to, pyrrole, imidazole, pyrazole, oxazole,thiazole and triazole rings.

Examples of the rings of the unsaturated Z groups of formula (III) abovemay include, but are not limited to, pyridine, pyrimidine, pyrazine,oxazine and triazine rings.

The compounds of formula (I), according to the invention, are preferablychosen from:

1-(2-(2-amino-4-hydroxyphenylamino)ethyl)-3-methyl-3H-imidazol-1-iumchloride;

1-{2-((3-amino-4-methylaminophenyl)methylamino)]ethyl}-3-methyl-3H-imidazol-1-iumchloride;

1-{2-((3-amino-4-methylaminophenyl)methylamino)ethyl}-1,4-dimethyl-1-piperaziniumchloride;

{2-((3-amino-4-methylaminophenyl)methylamino)ethyl}-triethylammoniumchloride;

1-(2-(2-amino-4-hydroxyphenylamino)ethyl)-1,4-dimethyl-1-piperaziniumchloride;

(2-{2-amino-4-(bis(2-hydroxyethyl)amino)phenylamino}-ethyl)diethylmethylammoniumchloride;

3-(3-{3-(3-(3-methyl-3H-imidazol-1-ium)propylamino)-4-aminophenylamino}propyl)-1-methyl-3H-imidazol-1-iumdichloride;

3-methyl-1-(2-(2,4,5-trihydroxyphenylamino)ethyl)-3H-imidazol-1-iumchloride;

1-(2-(2-amino-5-ethoxy-4-hydroxyphenylamino)ethyl)-3-methyl-3H-imidazol-1-iumchloride;

1-(2-(2-amino-5-hydroxy-4-methoxyphenylamino)ethyl)-3-methyl-3H-imidazol-iumchloride;

1-(2-{4-amino-5-(2-(diethylmethylammonium)ethylamino)-2-hydroxyphenoxy}ethyl)-3-methyl-3H-imidazol-1-iumdichloride; and acid addition salts thereof.

The acid addition salts for the compounds of formula (I), in accordancewith the invention, are preferably chosen from hydrochlorides,hydrobromides, sulphates, citrates, succinates, tartrates, lactates andacetates.

The compounds of formula (I), in accordance with the invention, can beeasily obtained according to methods that are well known in the art, byreduction of the corresponding cationic nitro compounds.

This reduction step (production of a primary aromatic amine), which mayor may not be followed by a salification step, is generally, forconvenience, the final step of the synthesis.

This reduction can take place earlier in the sequence of reactionsleading to the preparation of the compounds of formula (I), and,according to well-known processes, it is then necessary to “protect” theprimary amine created (for example by an acetylation,benzenesulphonation, etc. step), then to carry out the desiredsubstitution(s) or modification(s) (including quaternization) and to endby “deprotecting” (generally in acidic medium) the amine function.

Similarly, the phenolic function can be protected according towell-known processes, with a benzyl radical (“deprotection” by catalyticreduction) or with an ram acetyl or mesyl radical (“deprotection” inacidic medium).

When the synthesis is complete, the compounds of formula (I), inaccordance with the invention, may, if necessary, be recovered bymethods which are well known in the art, such as crystallization ordistillation.

Another subject of the invention is the use of the compounds of formula(I), in accordance with the invention, as oxidation-dye precursors forthe oxidation-dyeing of keratin fibers, and in particular of humankeratin fibers, such as hair.

The invention also relates to a composition for the oxidation-dyeing ofkeratin fibers, and in particular of human keratin fibers such as thehair, characterized in that it comprises, as oxidation-dye precursor, ina medium which is suitable for dyeing, at least one compound of formula(I), in accordance with the invention.

The compound(s) of formula (I) in accordance with the inventionpreferably represent(s) from 0.0005 to 12% by weight approximatelyrelative to the total weight of the dye composition, and even morepreferably from 0.005 to 6% by weight approximately relative to thisweight.

The medium which is suitable for dyeing (or the support), generallycomprises of water or a mixture of water and at least one organicsolvent to dissolve the compounds which would not be sufficientlysoluble in water. Examples of organic solvents may include, but are notlimited to, (C₁-C₄)lower alkanols, such as ethanol and isopropanol;glycerol; glycols and glycol ethers, such as 2-butoxyethanol, propyleneglycol, propylene glycol monomethyl ether, diethylene glycol monoethylether and monomethyl ether, as well as aromatic alcohols, such as benzylalcohol or phenoxyethanol, similar products and mixtures thereof.

The solvents may be present in proportions preferably ranging from 1 to40% by weight approximately relative to the total weight of the dyecomposition, and even more preferably ranging from 5 to 30% by weightapproximately.

The pH of the dye composition, in accordance with the invention, rangesfrom 3 to 12 approximately, and preferably ranges from 5 to11approximately. It can be adjusted to the desired value using acidifyingor basifying agents commonly used to dye keratin fibers.

Examples of acidifying agents may include, but are not limited to,inorganic or organic acids, such as hydrochloric acid, orthophosphoricacid, sulphuric acid, and carboxylic acids, such as acetic acid,tartaric acid, citric acid and lactic acid, and sulphonic acids.

Examples of basifying agents may include, but are not limited to,aqueous ammonia, alkaline carbonates, alkanolamines, such as mono-, di-and triethanolamine and derivatives thereof, sodium hydroxide, potassiumhydroxide and the compounds of formula (V) below:

in which W is a propylene residue optionally substituted with a hydroxylgroup or a (C₁-C₆)alkyl radical; R₁₄, R₁₅, R₁₆ and R₁₇, which may beidentical or different, are chosen from a hydrogen atom, a (C₁-C₆)alkylradical or a hydroxy (C₁-C₆)alkyl radical.

In addition to the compound(s) of formula (I) defined above, the dyecomposition, in accordance with the invention, can also contain at leastone oxidation base which can be chosen from the oxidation basesconventionally used for oxidation-dyeing and may include, but are notlimited to, para-phenylenediamines, bis(phenyl)alkylenediamines,para-aminophenols, ortho-aminophenols and heterocyclic bases.

Examples of para-phenylenediamines may include, but are not limited to,para-phenylenediamine, para-toluylenediamine,2,6-dimethyl-para-phenylenediamine,2-β-hydroxyethyl-para-phenylenediamine,2-n-propyl-para-phenylenediamine, 2-isopropyl-para-phenylenediamine,N-(β-hydroxypropyl)-para-phenylenediamine,N,N-bis(β-hydroxyethyl)-para-phenylenediamine,4-amino-N-(β-methoxyethyl)aniline, the para-phenylenediamines describedin French patent application FR 2 630 438, the disclosure of which ishereby incorporated by reference, and acid addition salts thereof.

Examples of bis(phenyl)alkylenediamines may include, but are not limitedto,N,N′-bis(b-hydroxyethyl)-N,N′-bis(4′-aminophenyl)-1,3-diaminopropanol,N,N′-bis(b-hydroxyethyl)-N,N′-bis(4′-aminophenyl)ethylenediamine,N,N′-bis (4-aminophenyl)tetramethylenediamine,N,N′-bis(b-hydroxyethyl)-N,N′-bis (4-aminophenyl)tetramethylenediamine,N,N′-bis (4-methylaminophenyl)tetramethylenediamine andN,N′-bis(ethyl)-N,N′-bis(4′-amino-3′-methylphenyl)ethylenediamine andacid addition salts thereof.

Examples of para-aminophenols may include, but are not limited to,para-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluorophenol,4-amino-3-hydroxymethylphenol, 4-amino-2-methylphenol,4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethylphenol,4-amino-2-aminomethylphenol and4-amino-2-(β-hydroxyethylaminomethyl)phenol and acid addition saltsthereof.

Examples of ortho-aminophenols may include, but are not limited to,2-aminophenol, 2-amino-5-methylphenol, 2-amino-6-methylphenol and5-acetamido-2-aminophenol, and the acid addition salts thereof.

Examples of heterocyclic bases may include, but are not limited to,pyridine derivatives and pyrimidine derivatives that are non-cationic,and pyrazole derivatives.

Examples of pyridine derivatives may include, but are not limited to thecompounds described, for example, in GB patents 1 026 978 and 1 153 196,the disclosures of which are hereby incorporated by reference, such as2,5-diaminopyridine, 2-(4-methoxyphenyl)amino-3-aminopyridine,2,3-diamino-6-methoxypyridine,2-(β-methoxyethyl)amino-3-amino-6-methoxypyridine and3,4-diaminopyridine, and acid addition salts thereof.

Examples of pyrimidine derivatives may include, but are not limited tothe compounds described, for example, in German patent DE 2 359 399,Japanese patents JP 88-169 571 and 91-10659, or patent application WO96/15765, the disclosures of which are hereby incorporated by reference,such as 2,4,5,6-tetraaminopyrimidine,4-hydroxy-2,5,6-triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine,2,4-dihydroxy-5,6-diaminopyrimidine, 2,5,6-triaminopyrimidine andpyrazolopyrimidine derivatives such as those mentioned in patentapplication FR-A-2 750 048, the disclosure of which is herebyincorporated by reference, and among which mention may be made ofpyrazolo(1,5-a)pyrimidine-3,7-diamine;2,5-dimethylpyrazolo(1,5-a)pyrimidine-3,7-diamine;pyrazolo(1,5-a)pyrimidine-3,5-diamine;2,7-dimethylpyrazolo(1,5-a)pyrimidine-3,5-diamine;3-aminopyrazolo(1,5-a)pyrimidin-7-ol;3-aminopyrazolo(1,5-a)pyrimidin-5-0l;2-(3-aminopyrazolo(1,5-a)pyrimidin-7-ylamino)ethanol,2-(7-aminopyrazolo(1,5-a)pyrimidin-3-ylamino)ethanol,2-((3-aminopyrazolo(1,5-a)pyrimidin-7-yl)-(2-hydroxyethyl)amino)ethanol,2-((7-aminopyrazolo(1,5-a)pyrimidin-3-yl)-(2-hydroxyethyl)amino)ethanol,5,6-dimethylpyrazolo(1,5-a)pyrimidine-3,7-diamine,2,6-dimethylpyrazolo(1,5-a)pyrimidine-3,7-diamine,2,5,N7,N7-tetramethylpyrazolo(1,5-a)pyrimidine-3,7-diamine and3-amino-5-methyl-7-imidazolylpropylaminopyrazolo(1,5-a)pyrimidine, acidaddition salts thereof and the tautomeric forms thereof when atautomeric equilibrium exists.

Examples of pyrazole derivatives may include, but are not limited to thecompounds described in patents DE 3 843 892 and DE 4 133 957 and patentapplications WO 94/08969, WO 94/08970, FR-A-2 733 749 and DE 195 43 988,the disclosures of all of which are hereby incorporated by reference,such as 4,5-diamino-1-methylpyrazole, 3,4-diaminopyrazole,4,5-diamino-1-(4′-chlorobenzyl)pyrazole,4,5-diamino-1,3-dimethylpyrazole, 4,5-diamino-3-methyl-1-phenylpyrazole,4,5-diamino-1-methyl-3-phenylpyrazole,4-amino-1,3-dimethyl-5-hydrazinopyrazole,1-benzyl-4,5-diamino-3-methylpyrazole,4,5-diamino-3-tert-butyl-1-methylpyrazole,4,5-diamino-1-tert-butyl-3-methylpyrazole,4,5-diamino-1-(β-hydroxyethyl)-3-methylpyrazole,4,5-diamino-1-ethyl-3-methylpyrazole,4,5-diamino-1-ethyl-3-(4′-methoxyphenyl)pyrazole,4,5-diamino-1-ethyl-3-hydroxymethylpyrazole,4,5-diamino-3-hydroxymethyl-1-methylpyrazole,4,5-diamino-3-hydroxymethyl-1-isopropylpyrazole,4,5-diamino-3-methyl-1-isopropylpyrazole,4-amino-5-(2′-aminoethyl)amino-1,3-dimethylpyrazole,3,4,5-triaminopyrazole, 1-methyl-3,4,5-triaminopyrazole,3,5-diamino-1-methyl-4-methylaminopyrazole and3,5-diamino-4-(β-hydroxyethyl)amino-1-methylpyrazole, and acid additionsalts thereof.

When they are used, these oxidation bases preferably represent from0.0005 to 12% by weight approximately relative to the total weight ofthe dye composition and even more preferably from 0.005 to 6%approximately relative to this weight.

The oxidation-dye compositions, in accordance with the invention, mayalso comprise at least one coupler and/or at least one direct dye, inparticular to modify the shades or to enrich them with glints.

The couplers, which can be used in the oxidation-dye compositions, inaccordance with the invention, may be chosen from the couplersconventionally used for oxidation-dyeing and may include, but are notlimited to, meta-phenylenediamines, meta-aminophenols, meta-diphenolsand heterocyclic couplers such as, for example, indole derivatives,indoline derivatives, pyridine derivatives, pyrazoloazoles andpyrazolones, and acid addition salts thereof.

These couplers may also be chosen from 2-methyl-5-aminophenol,5-N-(β-hydroxyethyl)amino-2-methylphenol, 3-aminophenol,1,3-dihydroxybenzene, 1,3-dihydroxy-2-methylbenzene,4-chloro-1,3-dihydroxybenzene, 2,4-diamino-1-(β-hydroxyethyloxy)benzene,2-amino-4-(β-hydroxyethylamino)-1-methoxybenzene, 1,3-diaminobenzene,1,3-bis(2,4-diaminophenoxy)propane, sesamol, α-naphthol,6-hydroxyindole, 4-hydroxyindole, 4-hydroxy-N-methylindole,6-hydroxyindoline, 2,6-dihydroxy-4-methylpyridine,1H-3-methylpyrazol-5-one, 1-phenyl-3-methylpyrazol-5-one and3,6-dimethylpyrazolo(3,2-c)-1,2,4-triazole, and acid addition saltsthereof.

When they are present, these couplers preferably represent from 0.0001to 10% by weight approximately relative to the total weight of the dyecomposition and even more preferably from 0.005 to 5% by weightapproximately relative to this weight.

In general, acid addition salts, which can be used in the context of theinvention (compounds of formula (I), oxidation bases and couplers), maybe chosen from hydrochlorides, hydrobromides, sulphates, citrates,succinates, tartrates, lactates and acetates.

The dye composition, in accordance with the invention, may also comprisevarious adjuvants conventionally used in compositions for dyeing thehair, such as anionic, cationic, nonionic, amphoteric or zwitterionicsurfactants or mixtures thereof, anionic, cationic, nonionic, amphotericor zwitterionic polymers or mixtures thereof, inorganic or organicthickeners, antioxidants, penetration agents, sequestering agents,fragrances, buffers, dispersing agents, packaging agents, such as, forexample, silicones, film-forming agents, preserving agents andopacifiers.

One of ordinary skill in the art will know how to select this or theseoptional additional compounds such that the advantageous propertiesintrinsically associated with the oxidation-dye composition, inaccordance with the invention, are not, or are not substantially,adversely affected by the addition(s) envisaged.

The dye composition, according to the invention, may be in variousforms, such as in the form of liquids, creams or gels, or in any otherform which is suitable for dyeing keratin fibers, in particular humanhair.

The invention also relates to a process for dyeing keratin fibers, inparticular human keratin fibers, such as hair, using the dyecomposition, as defined above.

According to this process, at least one dye composition, as definedabove, is applied to the fibers for a period which is sufficient todevelop the desired coloration, either in air or using an oxidizingagent. The dye composition may optionally comprise oxidation catalysts,in order to accelerate the oxidation process.

According to a first embodiment of the process of the invention, thecoloration of the fibers may be carried out without addition of anoxidizing agent, merely on contact with atmospheric oxygen.

According to a second embodiment of the process of the invention, inparticular when the dye composition, in accordance with the invention,comprises one or more oxidation bases and/or one or more couplers, atleast one dye composition, as defined above, is applied to the fibers,the color being developed at acidic, neutral or alkaline pH using anoxidizing agent which is added to the dye composition just at the timeof use, or which is present in an oxidizing composition which is appliedsimultaneously or sequentially in a separate manner.

According to this second embodiment of the dyeing process of theinvention, the dye composition, described above, is preferably mixed, atthe time of use, with an oxidizing composition comprising, in a mediumwhich is suitable for dyeing, at least one oxidizing agent present in anamount which is sufficient to develop a coloration. The mixture obtainedis then applied to the keratin fibers and is left in place for 3 to 50minutes approximately, preferably 5 to 30 minutes approximately, afterwhich the fibers are rinsed, washed with shampoo, rinsed again anddried.

The oxidizing agent present in the oxidizing composition, as definedabove, may be chosen from the oxidizing agents conventionally used forthe oxidation-dyeing of keratin fibers, and may include, but are notlimited to, hydrogen peroxide, urea peroxide, alkali metal bromates andpersalts, such as perborates and persulphates, and enzymes, such asperoxidases, laccases, tyrosinases and oxidoreductases, which mayinclude, but are not limited to, pyranose oxidases, glucose oxidases,glycerol oxidases, lactate oxidases, pyruvate oxidases and uricases.

The pH of the oxidizing composition comprising the oxidizing agent, asdefined above, is such that, after mixing with the dye composition, thepH of the resultant composition applied to the keratin fibers preferablyvaries from 3 to 12 approximately, and even more preferably from 5 to11. It is adjusted to the desired value using acidifying or basifyingagents commonly used to dye keratin fibers and as defined above.

The oxidizing composition, as defined above, may also comprise variousadjuvants conventionally used in compositions for dyeing the hair and asdefined above.

The composition, which is finally applied to the keratin fibers, may bein various forms, such as in the form of liquids, creams, gels or anyother form which is suitable for dyeing keratin fibers, in particularhuman hair.

Another subject of the invention is a multi-compartment dyeing device or“kit” or any other multi-compartment packaging system, a firstcompartment of which contains the dye composition, as defined above, anda second compartment of which comprises the oxidizing composition, asdefined above. These devices can be equipped with a means for deliveringthe desired mixture onto the hair, such as the devices described inpatent FR 2,586,913, the disclosure of which is hereby incorporated byreference.

The examples which follow are intended to illustrate the inventionwithout, however, limiting its scope.

PREPARATION EXAMPLES Preparation Example 1 Synthesis of1-(2-(2-amino-4-hydroxyphenylamino)ethyl)-3-methyl-3H-imidazol-1-iumchloride dihydrochloride

a) Preparation of 2-(4-benzyloxy-2-nitrophenylamino)ethanol

A suspension of 115 g (0.58 mol) of4-(2-hydroxyethylamino)-3-nitrophenol (RN 65235-31-6) and 96.2 g (0.696mol) of potassium carbonate in 350 ml of dimethylformamide was preparedand heated in a boiling water bath.

73.6 ml (0.638 mol) of benzyl chloride were added dropwise over 20minutes and heating was continued for 3 hours in a boiling water bath.

The resulting mixture was poured into 2 litres of ice-cold water and thecrystalline product was spin-dried and reslurried in water.

After recrystallization from refluxing 96° ethanol, 145 g of red-browncrystals of 2-(4-benzyloxy-2-nitrophenylamino)ethanol melting at 112° C.(Kofler) were obtained, the elemental analysis of which, calculated forC₁₅H₁₆N₂O₄, was:

% C H N O Calculated 62.49 5.59 9.72 22.20 Found 62.45 5.61 9.60 22.35

b) Preparation of (4-benzyloxy-2-nitrophenyl)-(2-chloroethyl)amine

144.5 g (0.5 mol) of 2-(4-benzyloxy-2-nitrophenylamino)ethanol obtainedabove in the previous step and 97 ml of triethylamine (0.7 mol) weredissolved in 750 ml of dimethylformamide and cooled to 0° C.

58.0 ml (0.6 mol) of methanesulphonyl chloride were added dropwise over40 minutes while maintaining the temperature between 0 and 5° C.

The resulting mixture was stirred at a temperature of 0° C. for afurther 30 minutes.

63.5 g (1.5 mol) of lithium chloride were added and the mixture wasplaced in a boiling water bath for 15 minutes.

The resulting mixture was poured into 2.5 litres of ice-cold water andan oily precipitate crystallized slowly.

This product was spin-dried, reslurried in water and dried.

After recrystallization from refluxing isopropyl acetate, 102.3 g ofbrick-coloured crystals of(4-benzyloxy-2-nitrophenyl)-(2-chloroethyl)amine melting at 83° C.(Kofler) were obtained, the elemental analysis of which, calculated forC₁₅H₁₅N₂O₃Cl, was:

% C H N O Cl Calculated 58.73 4.93 9.13 15.91 11.56 Found 58.67 4.849.13 15.65 11.20

c) Preparation of1-(2-(4-benzyloxy-2-nitrophenylamino)ethyl)-3-methyl-3H-imidazol-1-iumchloride monohydrate

30.6 g (0.1 mol) of (4-benzyloxy-2-nitrophenyl)-(2-chloroethyl)amineobtained above in the previous step and 24.6 g (0.3 mol) of1-methyl-1H-imidazole (RN 616-47-7) in 60 ml of toluene were refluxedfor 12 hours.

The resulting mixture was cooled and the crystalline precipitate wasspin-dried and reslurried in ethyl acetate.

After recrystallization from refluxing absolute ethanol, 27.2 g oforange-red crystals of1-(2-(4-benzyloxy-2-nitrophenylamino)ethyl)-3-methyl-3H-imidazol-1-iumchloride monohydrate melting at 145° C. (Kofler) were obtained, theelemental analysis of which, calculated for C₁₉H₂₁N₄O₃Cl.H₂O, was:

% C H N O Cl Calculated 56.09 5.70 13.77 15.73 8.71 Found 57.29 5.6913.88 15.10 8.66

d) Reduction and debenzylation of1-(2-(4-benzyloxy-2-nitrophenylamino)ethyl)-3-methyl-3H-imidazol-1-iumchloride monohydrate

15.3 g (0.0376 mol) of1-(2-(4-benzyloxy-2-nitrophenylamino)ethyl)-3-methyl-3H-imidazol-1-iumchloride monohydrate obtained above in the previous step, 5 g of 5%palladium-on-charcoal (containing 50% water), 150 ml of 96° ethanol and150 ml of water were placed in a hydrogenator.

The reduction took place in ½ hour at a hydrogen pressure of about 8 barand at a temperature which was gradually raised to 45° C. Afterfiltering off the catalyst under nitrogen, the filtrate was poured into25 ml of 36% hydrochloric acid and evaporated to dryness under reducedpressure.

After recrystallization from a refluxing ethanol/water mixture anddrying at 40° C. under vacuum and over potassium hydroxide, 8.0 g ofbeige-coloured crystals of1-(2-(2-amino-4-hydroxyphenylamino)ethyl)-3-methyl-3H-imidazol-1-iumchloride dihydrochloride melting with decomposition at 220-222° C.(Kofler) were obtained, the elemental analysis of which, calculated forC₁₂H₁₉N₄OCl₃, was:

% C H N O Cl Calculated 42.19 5.61 16.40 4.68 31.13 Found 41.95 5.6916.13 5.63 30.62

Preparation Example 2 Synthesis of1-{2-((3-amino-4-methylaminophenyl)methylamino)ethyl}-3-methyl-3H-imidazol-1-iumchloride dihydrochloride

a) Preparation of3-methyl-1-{2-(methyl-(4-methylamino-3-nitrophenyl)amino)ethyl}-3H-imidazol-1-iumchloride monohydrate

A suspension of 41.4 g (0.17 mol) ofN4-(2-chloroethyl)-N1,N4-dimethyl-2-nitrobenzene-1,4-diamine (RN14607-54-6) obtained above in the previous step and 41.8 g (0.51 mol) of1-methyl-1H-imidazole (RN 616-47-7) in 100 ml of toluene was prepared.

This suspension was heated with stirring at the reflux point of thetoluene for 4 hours and the boiling product was spin-dried andreslurried twice in ethyl acetate and then in absolute ethanol.

After drying at 40° C. under vacuum, 37.8 g of violet crystals of3-methyl-1-{2-(methyl-(4-methylamino-3-nitrophenyl)amino)ethyl}-3H-imidazol-1-iumchloride monohydrate melting at 135° C. (Kofler) were obtained, theelemental analysis of which, calculated for C₁₄H₂₀N₅O₂Cl.H₂O, was:

% C H N O Cl Calculated 48.91 6.45 20.37 13.96 10.31 Found 48.65 6.5020.29 14.00 10.28

b)Reduction of3-methyl-1-{2-(methyl-(4-methylamino-3-nitrophenyl)amino)ethyl}-3H-imidazol-1-iumchloride monohydrate

19.5 g (0.0567 mol) of3-methyl-1-{2-(methyl-(4-methylamino-3-nitrophenyl)amino)ethyl}-3H-imidazol-1-iumchloride monohydrate obtained above in the previous step, 10 g of 5%palladium-on-charcoal (containing 50% water), 200 ml of 96° ethanol and200 ml of water were placed in a hydrogenator.

The reduction took place in ½ hour at a hydrogen pressure of about 9 barand at a temperature which was gradually raised to 50° C. Afterfiltering off the catalyst under nitrogen, the filtrate was poured into20 ml of 36% hydrochloric acid and evaporated to dryness under reducedpressure.

The compound was taken up several times in absolute ethanol. Afterrecrystallization from a refluxing ethanol/water mixture and drying at40° C. under vacuum and over potassium hydroxide, 8.0 g of pale greycrystals of1-{2-((3-amino-4-methylaminophenyl)methylamino)ethyl}-3-methyl-3H-imidazol-1-iumchloride dihydrochloride melting with decomposition at 240-242° C.(Kofler) were obtained. The proton NMR spectrum of which was inaccordance with the proposed structure.

APPLICATION EXAMPLES Examples1 to 8 of Dyeing in Alkaline Medium

The dye compositions below, in accordance with the invention, wereprepared (contents in grams):

EXAMPLE 1 2 3 4 5 6 7 8 1-(2-(2-Amino-4-hydroxy- 1.02 1.02 1.02 1.021.02 1.02 1.02 1.02 phenylamino)ethyl)-3-methyl- 3H-imidazol-1-iumchloride dihydrochloride (compound of formula (I)) para-toluylenediamine0.33 — — — — — — — (oxidation base) para-aminophenol (oxidation — 0.327— — — — — — base) Pyrazolo-(1,5-a)pyrimidine- — — 0.666 — — — — —3,7-diamine dihydrochloride (oxidation base) 1,3-dihydroxybenzene — — —0.33 — — — — (coupler) 3-aminophenol (coupler) — — — — 0.327 — — —5-N-(β-Hydroxyethyl)amino- — — — — — 0.498 — — 2-methylphenol (coupler)2,4-diamino-1-(β-hydroxy- — — — — — — 0.723 — ethyloxy)benzene dihydro-chloride (coupler) 3,6-dimethylpyrazolo(3,2-c)- — — — — — — — 0.421,2,4-triazole (coupler) Common dye support No. 1 (*) (*) (*) (*) (*)(*) (*) (*) Demineralized water qs 100 g 100 g 100 g 100 g 100 g 100 g100 g 100 g

(*) Common dye support No. 1: -96° ethyl alcohol 18 g -Sodiummetabisulphite as an aqueous 0.68 g 35% solution -Pentasodium salt ofdiethylenetriamine- 1.1 g pentaacetic acid -20% aqueous ammonia 10.0 g

At the time of use, each of the above dye compositions were mixed,weight for weight with a 20-volume hydrogen peroxide solution (6% byweight) of pH 3.

The mixtures obtained were applied to locks of natural grey haircontaining 90% white hairs, for 30 minutes. The locks were then rinsed,washed with a standard shampoo, rinsed again and then dried.

The shades obtained are given in the table below:

EXAMPLE Dyeing pH Shade obtained 1 10 ± 0.2 Iridescent golden dark blond2 10 ± 0.2 Coppery golden dark blond 3 10 ± 0.2 Coppery iridescent lightchestnut 4 10 ± 0.2 Coppery iridescent dark blond 5 10 ± 0.2 Copperyiridescent dark blond 6 10 ± 0.2 Golden iridescent dark blond 7 10 ± 0.2Matet ash dark blond 8 10 ± 0.2 Iridescent golden dark blond

Examples 9 to 16 of Dyeing in Alkaline Medium

The dye compositions below, in accordance with the invention, wereprepared (contents in grams):

EXAMPLE 9 10 11 12 13 14 15 16 1-{2-[(3-Amino-4-methyl- 1.11 1.11 1.111.11 1.11 1.11 1.11 1.11 aminophenyl)methylamino]-ethyl}-3-methyl-3H-imidazol- 1-ium chloride dihydro- chloride (compoundof formula (I)) para-toluylenediamine 0.33 — — — — — — — (oxidationbase) para-aminophenol (oxidation — 0.327 — — — — — — base)Pyrazolo-[1,5-a]pyrimidine- — — 0.666 — — — — — 3,7-diaminedihydrochloride (oxidation base) 1,3-dihydroxybenzene — — — 0.33 — — — —(coupler) 3-aminophenol (coupler) — — — — 0.327 — — —5-N-(b-Hydroxyethyl)amino- — — — — — 0.498 — — 2-methylphenol (coupler)2,4-diamino-1-(b-hydroxy- — — — — — — 0.723 — ethyloxy)benzene dihydro-chloride (coupler) 3,6-dimethylpyrazolo[3,2-c]- — — — — — — — 0.421,2,4-triazole (coupler) Common dye support No. 1 (*) (*) (*) (*) (*)(*) (*) (*) Demineralized water qs 100 g 100 g 100 g 100 g 100 g 100 g100 g 100 g

(*) Common dye support No. 1: -96° ethyl alcohol 18 g -Sodiummetabisulphite as an aqueous 0.68 g 35% solution -Pentasodium salt ofdiethylenetriamine- 1.1 g pentaacetic acid -20% aqueous ammonia 10.0 g

At the time of use, each of the above dye compositions were mixed,weight for weight, with a 20-volume hydrogen peroxide solution (6% byweight) of pH 3.

The mixtures obtained were applied to locks of natural grey haircontaining 90% white hairs, for 30 minutes. The locks were then rinsed,washed with a standard shampoo, rinsed again and then dried.

The shades obtained are given in the table below:

EXAMPLE Dyeing pH Shade obtained 9 10 ± 0.2 Coppery iridescent darkblond 10 10 ± 0.2 Iridescent coppery blond 11 10 ± 0.2 Iridescent ashlight chestnut 12 10 ± 0.2 Mahogany iridescent blond 13 10 ± 0.2slightly iridescent ash light chestnut 14 10 ± 0.2 Bluish ash lightchestnut 15 10 ± 0.2 Bluish ash light chestnut 16 10 ± 0.2 Mahoganyiridescent blond

What is claimed is:
 1. A compound of formula (I) below, and acidaddition salts thereof:

in which: A₁, A₂ and A₃, which may be identical or different, are chosenfrom a group —NR₇R₈ and a hydroxyl radical; one and only one of thegroups A₁, A₂ and A₃ may also represent a group R₃ as defined below; R₁,R₂ and R₃, which may be identical or different, are chosen from ahydrogen atom; a halogen atom; a group Z as defined below; a(C₁-C₆)alkylcarbonyl radical; an amino(C₁-C₆)alkylcarbonyl radical; anN—Z-amino(C₁-C₆)alkylcarbonyl radical; anN—(C₁-C₆)alkylamino(C₁-C₆)alkylcarbonyl radical; anN,N-di(C₁-C₆)-alkylamino (C₁-C₆)alkylcarbonyl radical; anamino(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radical; anN—Z-amino(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radical; anN—(C₁-C₆)alkylamino(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radical; anN,N-di(C₁-C₆)alkylamino(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radical; acarboxyl radical; a (C₁-C₆)alkylcarboxyl radical; a(C₁-C₆)alkylsulphonyl radical; an aminosulphonyl radical; anN—Z-aminosulphonyl radical; a (C₁-C₆)N-alkylaminosulphonyl radical; anN,N-di(C₁-C₆)alkylaminosulphonyl radical; a (C₁-C₆)aminosulphonylalkylradical; a (C₁-C₆)N—Z-aminosulphonylalkyl radical; anN—(C₁-C₆)alkylaminosulphonyl(C₁-C₆)alkyl radical; an N,N-di(C₁-C₆)-alkylaminosulphonyl(C₁-C₆)alkyl radical; a carbamyl radical; anN—(C₁C₆)alkylcarbamyl radical, an N,N-di(C₁-C₆)alkylcarbamyl radical; acarbamyl(C₁-C₆)alkyl radical; an N—(C₁-C₆)alkylcarbamyl(C₁-C₆)alkylradical; an N,N-di(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radical; a(C₁-C₆)alkyl radical; a (C₁-C₆)monohydroxyalkyl radical; a(C₂-C₆)polyhydroxyalkyl radical; a (C₁-C₆)alkoxy(C₁-C₆)alkyl radical; a(C₁-C₆)trifluoroalkyl radical; a cyano radical; a group OR₆ or SR₆; anamino group protected by a (C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylcarboxyl,trifluoro(C₁-C₆)alkylcarbonyl, amino(C₁-C₆)alkylcarbonyl,N—Z-amino(C₁-C₆)alkylcarbonyl, N—(C₁-C₆)alkylamino(C₁-C₆)alkylcarbonyl,N,N-di(C₁-C₆)alkylamino(C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylcarboxyl,carbamyl, N—(C₁-C₆)alkylcarbamyl, N,N-di(C₁-C₆)alkylcarbamyl,(C₁-C₆)alkylsulphonyl, aminosulphonyl, N—Z-aminosulphonyl,(C₁-C₆)N-alkylaminosulphonyl, N,N-di(C₁-C₆)alkylaminosulphonyl,thiocarbamyl or formyl radical, or with a group Z as defined below inwhich a linker arm D comprises a ketone function directly attached tothe nitrogen atom of the amino group; and a (C₁-C₆)aminoalkyl radical inwhich the alkyl is unsubstituted or substituted with one or morehydroxyl radicals; a (C₁-C₆)aminoalkyl radical in which the alkyl isunsubstituted or substituted with one or more hydroxyl radicals and inwhich the amine is substituted with one or two radicals, which may beidentical or different, chosen from alkyl, (C₁-C₆)monohydroxyalkyl,(C₂-C₆)polyhydroxyalkyl, (C₁-C₆)alkylcarbonyl, cartamyl,N—(C₁-C₆)alkylcarbamyl, N,N-di(C₁-C₆)alkylcarbamyl, C₁-C₆alkylsulphonyl, formyl, trifluoro (C₁-C₆)-alkylcarbonyl,(C₁-C₆)alkylcarboxyl and thiocatamyl radicals, or from a group Z asdefined below, or which may form, together with the nitrogen atom towhich they are attached, a 5- or 6-membered ring which is carbon-basedor which contains one or more hetero atoms; R₆ is chosen from a(C₁-C₆)alkyl radical; a (C₁-C₆)monohydroxyalkyl radical; a(C₂-C₆)polyhydroxyalkyl radical; a group Z as defined below; a(C₁-C₆)alkoxy(C₁-C₆)alkyl radical; an aryl radical; a benzyl radical; acarboxy(C₁-C₆)alkyl radical; a (C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radical;a cyano(C₁-C₆)alkyl radical; a carbamyl(C₁-C₆)alkyl radical; anN—(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radical; anN,N-di(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radical; a (C₁-C₆)trifluoroalkylradical; a (C₁-C₆)aminosulphonylalkyl radical; a(C₁-C₆)N—Z-aminosulphonylalkyl radical; anN—(C₁-C₆)alkylaminosulphonyl(C₁-C₆)alkyl radical; anN,N-di(C₁-C₆)alkylaminosulphonyl(C₁-C₆)alkyl radical; a(C₁-C₆)alkylsulphinyl (C₁-C₆)alkyl radical; a(C₁-C₆)alkylsulphonyl(C₁-C₆)alkyl radical; a (C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radical; a (C₁-C₆)aminoalkyl radical in which the alkyl isunsubstituted or substituted with one or more hydroxyl radicals; and a(C₁-C₆)aminoalkyl radical in which the alkyl is unsubstituted orsubstituted with one or more hydroxyl radicals and in which the amine issubstituted with one or two identical or different radicals chosen from(C₁-C₆)alkyl, (C₁-C₆)monohydroxyalkyl, (C₂-C₆)polyhydroxyalkyl,(C₁-C₆)allkylcarbonyl, formyl, trifluoro(C₁-C₆)alkylcarbonyl,(C₁-C₆)alkylcarboxyl, carbamyl, N—(C₁-C₆)alkylcarbamyl,N,N-di(C₁-C₆)alkylcarbamyl, thiocarbamyl and (C₁-C₆)alkylsulphonylradicals, or from a group Z as defined below; or which may form,together with the nitrogen atom to which they are attached, a 5- or6-membered ring which is carbon-based or which contains one or morehetero atoms; R₄, R₅, R₇ and R₈, which may be Identical or different,are chosen from a hydrogen atom; a group Z as defined below, in whichthe linker arm D contains no ketone functions directly linked to thenitrogen atom bearing the radicals R₄ and R₅; a (C₁-C₆)alkyl radical; a(C₁-C₆)monohydroxyalkyl radical; a (C₂-C₆)polyhydroxyalkyl radical; a(C₁-C₆)alkoxy(C₁-C₆)alkyl radical; an aryl radical; a benzyl radical; acyano(C₁-C₆)alkyl radical; a carbamyl(C₁-C₆)alkyl radical; anN—(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radical; anN,N-di(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radical; athiocarbamyl(C₁-C₆)alkyl radical; a (C₁-C₆)trifluoroalkyl radical; a(C₁-C₆)sulphoalkyl radical; a (C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radical, a(C₁-C₆)alkylsulphinyl(C₁-C₆)alkyl radical; a (C₁-C₆)aminosulphonylalkylradical; a (C₁-C₆)N—Z-aminosulphonylalkyl radical; anN—(C₁-C₆)alkylaminosulphonyl(C₁-C₆)alkyl radical; anN,N-di(C₁-C₆)alkylaminosulphonyl(C₁-C₆)alkyl radical; a(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radical; a (C₁-C₆)aminoalkyl radical inwhich the alkyl is unsubstituted or substituted with one or morehydroxyl radicals; and a (C₁-C₆)aminoalkyl radical in which the alkyl isunsubstituted or substituted with one or more hydroxyl radicals and inwhich the amine is substituted with one or two identical or differentradicals chosen from (C₁-C₆)alkyl, (C₁-C₆)monohydroxyalkyl,(C₂-C₆)polyhydroxyalkyl, (C₁-C₆)alkylcarbonyl, carbamyl,N—(C₁-C₆)alkylcarbamyl, N,N-di(C₁-C₆)alkylcarbamyl,(C₁-C₆)alkylsulphonyl, formyl, trifluoro(C₁-C₆)alkylcarbonyl,(C₁-C₆)alkylcarboxyl and thiocarbamyl radicals, or from a group Z asdefined below; or which may form, together with the nitrogen atom towhich they are attached, a 5- or 6-membered ring which is carbon-basedor which contains one or more hetero atoms; Z is chosen from theunsaturated cationic groups of formulae (II) and (III) below, and thesaturated cationic groups of formula (IV) below:

in which: D is a linker arm which represents a linear or branched alkylchain, which can be interrupted by one or more hetero atoms, and whichcan be substituted with one or more hydroxyl or C₁-C₆ alkoxy radicals,and which can bear one or more ketone functions; the ring members E, G,J, L and M, which may be identical or different, are chosen from acarbon, oxygen, sulphur and nitrogen; n is an integer ranging from 0 to4; m is an integer ranging from 0 to 5; the R radical, which may beidentical or different, are chosen from a second Z group, which isidentical to or different from the first Z group, a halogen atom, ahydroxyl radical, a (C₁-C₆)alkyl radical, a (C₁-C₆)monohydroxyalkylradical, a (C₂-C₆)polyhydroxyalkyl radical, a nitro radical, a cyanoradical, a cyano(C₁-C₆)alkyl radical, a (C₁-C₆)alkoxy radical, atri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radical, an amido radical, a formylradical, a carboxyl radical, a (C₁-C₆)alkylcarbonyl radical, a thioradical, a (C₁-C₆)thioalkyl radical, a (C₁-C₆)alkylthio radical, anamino radical, an amino radical protected with a (C₁-C₆)alkylcarbonyl,carbamyl or (C₁-C₆)alkylsulphonyl radical; a group NHRO or NROR″ inwhich RO and R″, which may be identical or different, are chosen from a(C₁-C₆)alkyl radical, a (C₁-C₆)monohydroxyalkyl radical and a(C₂-C₆)polyhydroxyalkyl radical; R₉ is chosen from a (C₁-C₆)alkylradical, a (C₁-C₆)monohydroxyalkyl radical, a (C₂-C₆)polyhydroxyalkylradical, a cyano(C₁-C₆)alkyl radical, atri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radical, a (C₁-C₆)alkoxy(C₁-C₆)alkylradical, a carbamyl-(C₁-C₆)alkyl radical, a(C₁-C₆)alkylcarboxy(C₁-C₆)-alkyl radical, a benzyl radical and a secondZ group, which is identical to or different from the first Z group; R₁₀,R₁₁ and R₁₂, which may be identical or different, are chosen from a(C₁-C₆)alkyl radical, a (C₁-C₆)monohydroxyalkyl radical, a(C₂-C₆)polyhydroxyalkyl radical, a (C₁-C₆)alkoxy(C₁-C₆)alkyl radical, acyano(C₁-C₆)alkyl radical, an aryl radical, a benzyl radical, a(C₁-C₆)amidoalkyl radical, a tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicaland a (C₁-C₆)aminoalkyl radical in which the amine is protected by a(C₁-C₆)alkylcarbonyl, carbamyl or (C₁-C₆)alkylsulphonyl radical; two ofthe R₁₀, R₁₁ and R₁₂ radicals may also together form, with the nitrogenatom to which they are attached, a carbonaceous saturated 5- or6-membered ring or which contains one or more hetero atoms, wherein saidring may be unsubstituted or substituted with a halogen atom, a hydroxylradical, a (C₁-C₆)alkyl radical, a (C₁-C₆)monohydroxyalkyl radical, a(C₂-C₆)polyhydroxyalkyl radical, a nitro radical, a cyano radical, acyano(C₁-C₆)alkyl radical, a (C₁-C₆)alkoxy radical, atri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radical, an amido radical, a formylradical, a carboxyl radical, a keto(C₁-C₆)alkyl radical, a thio radical,a (C₁-C₆)thioalkyl radical, a (C₁-C₆)alkylthio radical, an amino radicalor an amino radical protected with a (C₁-C₆)alkylcarbonyl, carbamyl or(C₁-C₆)alkylsulphonyl radical; one of the R₁₀, R₁₁ and R₁₂ radicals mayalso be chosen from a second Z group which is identical to or differentfrom the first Z group; R₁₃ is chosen from a (C₁-C₆)alkyl radical; a(C₁-C₆)monohydroxy-alkyl radical; a (C₂-C₆)polyhydroxyalkyl radical; anaryl radical; a benzyl radical: a (C₁-C₆)aminoalkyl radical, a(C₁-C₆)aminoalkyl radical in which the amine is protected by a(C₁-C₆)alkylcarbonyl, carbamyl or (C₁-C₆)alkylsulphonyl radical; acarboxy(C₁-C₆)alkyl radical; a cyano(C₁-C₆)alkyl radical; acarbamyl(C₁-C₆)alkyl radical a (C₁-C₆)trifluoroalkyl radical; atri(C₁-C₆)alkyolsilane-(C₁-C₆)alkyl radical; a (C₁-C₆)sulphonamidoalkylradical; a (C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radical, a(C₁-C₆)alkylsulphinyl(C₁-C₆)alkyl radical; a(C₁-C₆)alkylsulphonyl(C₁-C₆)alkyl radical; a(C₁-C₆)alkylketo(C₁-C₆)alkyl radical; anN—(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radical, and anN—(C₁-C₆)alkylsulphonamido(C₁-C₆)alkyl radical; a and y are integersequal to 0 or 1; with the following conditions, in the unsaturatedcationic groups of formula (II): when a 0, the linker arm D is attachedto the nitrogen atom, when a=1, the linker arm D is attached to one ofthe ring members E, G, J or L vertices, y can take the value 1 only: 1)when the ring members E, G, J and L simultaneously represent a carbonatom and when the R₉ radical is carried by the nitrogen atom of theunsaturated ring; or alternatively 2) when at least one of the ringmembers E, G, J and L represents a nitrogen atom to which the R₉ radicalis attached; in the unsaturated cationic groups of formula (III): whena=0, the linker arm D is attached to the nitrogen atom, when a=1, thelinker arm D is attached to one of the ring members E, G, J, L or M, ycan take the value 1 only when at least one of the ring members E, G, J,L and M represents a divalent atom and when the R₉ radical is carried bythe nitrogen atom of the unsaturated ring; in the cationic groups offormula (IV): when a=0, then the linker arm D is attached to thenitrogen atom carrying the R₁₀ to R₁₂ radicals, when a=1, then two ofthe R₁₀ to R₁₂ radicals form, together with the nitrogen atom to whichthey are attached, a saturated 5- or 6membered ring as defined above,and the linker arm D is carried by a carbon atom of the saturated ring;X⁻ is a monovalent or divalent anion; with the proviso that the numberof cationic Z groups in the compound of formula (I) is at least equalto
 1. 2. The compound according to claim 1, wherein in at least one ofsaid formulae (II), (III), and (IV), D is a linear or branched alkylchain containing from 1 to 14 carbon atoms.
 3. The compound according toclaim 1, wherein in at least one of said formulae (II), (III), and (IV),D can be interrupted by oxygen, sulphur, or nitrogen atoms.
 4. Thecompound according to claim 1, wherein the rings of the unsaturated Zgroups of formula (II) are chosen from pyrrole, imidazole, pyrazole,oxazole, thiazole and triazole rings.
 5. The compound according to claim1, wherein the rings of the unsaturated Z groups of formula (III) arechosen from pyridine, pyrimidine, pyrazine, oxazine and triazine rings.6. The compound according to claim 1, wherein two of the R₁₀, R₁₁, andR₁₂ radicals form a pyrrolidine ring, a piperidine ring, a piperazinering or a morpholine ring, it being possible for the ring to beunsubstituted or substituted with a halogen atom, a hydroxyl radical, a(C₁-C₆)alkyl radical, a (C₁-C₆)monohydroxyalkyl radical, a (C₂-C₆)polyhydroxyalkyl radical, a nitro radical, a cyano radical, acyano(C₁-C₆)alkyl radical, a (C₁-C₆)alkoxy radical, atri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radical, an amido radical, a formylradical, a carboxyl radical, a keto(C₁-C₆)alkyl radical, a thio radical,a (C₁-C₆)thioalkyl radical, a (C₁-C₆)alkylthio radical, an amino radicalor an amino radical protected by a (C₁-C₆)alkylcarbonyl, carbamyl or(C₁-C₆)alkylsulphonyl radical.
 7. The compound according to claim 1,wherein X⁻ is chosen from a halogen atom, a hydroxide, a hydrogensulphate or a (C₁-C₆)alkyl sulphate.
 8. The compound according to claim1, wherein the compound is chosen from:1-(2-(2-amino-4-hydroxyphenylamino)ethyl)-3-methyl-3H-imidazol-1-iumchloride;1-{2-((3-amino-4-methylaminophenyl)methylamino)ethyl}-3-methyl-3H-imidazol-1-iumchloride;1-{2-((3-amino-4-methylaminophenyl)methylamino)ethyl}-1,4-dimethyl-1-piperaziniumchloride;{2-((3-amino-4-methylaminophenyl)methylamino)ethyl}-triethylammoniumchloride;1-(2-(2-amino-4-hydroxyphenylamino)ethyl)-1,4-dimethyl-1-piperaziniumchloride;(2-{2-amino-4-(bis(2-hydroxyethyl)amino)phenylamino}-ethyl)diethylmethylammoniumchloride;3-(3-{3-(3-(3-methyl-3H-imidazo1-ium)propylamino)-4-aminophenylamino}propyl)-1-methyl-3H-imidazol-1-iumdichloride;3-methyl-1-(2-(2,4,5-trihydroxyphenylamino)ethyl)-3H-imidazol-1-iumchloride;1-(2-(2-amino-5-ethoxy-4-hydroxyphenylamino)ethyl)-3-methyl-3H-imidazol-1-iumchloride;1-(2-(2-amino-5-hydroxy-4-methoxyphenylamino)ethyl)-3-methyl-3H-imidazol-1-iumchloride;1-(2-{4-amino-5-(2-(diethylmethylammonium)ethylamino)-2-hydroxyphenoxy}ethyl)-3-methyl-3H-imidazol-1-iumdichloride; and acid addition salts thereof.
 9. The compound accordingto claim 1, wherein acid addition salts are chosen from hydrochlorides,hydrobromides, sulphates, citrates, succinates, tartrates, lactates andacetates.
 10. A composition for the oxidation-dyeing of keratin fibers,comprising, in a medium which is suitable for dyeing, at least onecompound of formula (I) or an acid addition salt thereof as an oxidationdye precursor:

in which: A₁, A₂ and A₃, which may be identical or different, are chosenfrom a group —NR₇R₈ and a hydroxyl radical; one and only one of thegroups A₁, A₂ and A₃ may also represent a group R₃ as defined below; R₁,R₂ and R₃, which may be identical or different, are chosen from ahydrogen atom; a halogen atom; a group Z as defined below; a(C₁-C₆)alkylcarbonyl radical; an amino(C₁-C₆)alkylcarbonyl radical; anN—Z-amino(C₁-C₆)alkylcarbonyl radical; anN—(C₁-C₆)alkylamino(C₁-C₆)alkylcarbonyl radical; anN,N-di(C₁-C₆)-alkylamino(C₁-C₆)alkylcarbonyl radical; anamino(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radical; anN—Z-amino(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radical; anN—(C₁-C₆)alkylamino(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radical; anN,N-di(C₁-C₆)alkylamino(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radical; acarboxyl radical; a (C₁-C₆)alkylcarboxyl radical; a(C₁-C₆)alkylsulphonyl radical; an aminosulphonyl radical; anN—Z-aminosulphonyl radical; a (C₁-C₆)N-alkylaminosulphonyl radical; anN,N-di(C₁-C₆)alkylaminosulphonyl radical; a (C₁-C₆)aminosulphonylalkylradical; a (C₁-C₆)N—Z-aminosulphonylalkyl radical; anN—(C₁-C₆)alkylaminosulphonyl(C₁-C₆)alkyl radical; an N,N-di(C₁-C₆)-alkylaminosulphonyl(C₁-C₆)alkyl radical; a carbamyl radical;an N—(C₁-C₆)alkylcarbamyl radical; an N,N-di(C₁-C₆)alkylcarbamylradical; a carbamyl(C₁-C₆)alkyl radical; anN—(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radical; anN,N-di(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radical; a (C₁-C₆)alkyl radical;a (C₁-C₆)monohydroxyalkyl radical; a (C₂-C₆)polyhydroxyalkyl radical; a(C₁-C₆)alkoxy(C₁-C₆)alkyl radical; a (C₁-C₆)trifluoroalkyl radical; acyano radical; a group OR₆ or SR₆; an amino group protected by a(C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylcarboxyltrifluoro(C₁-C₆)alkylcarbonyl, amino(C₁-C₆)alkylcarbonyl,N—Z-amino(C₁-C₆)alkylcarbonyl, N—(C₁-C₆)alkylamino(C₁-C₆)alkylcarbonyl,N,N-di(C₁-C₆)alkylamino(C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylcarboxyl,carbamyl, N—(C₁-C₆)alkylcarbamyl, N,N-di(C₁-C₆)alkylcarbamyl,(C₁-C₆)alkylsulphonyl, aminosulphonyl, N—Z-aminosulphonyl,(C₁-C₆)N-alkylaminosulphonyl, N,N-di(C₁-C₆)alkylaminosulphonyl,thiocarbamyl or formyl radical, or with a group Z as defined below inwhich a linker arm D comprises a ketone function directly attached tothe nitrogen atom of the amino group; and a (C₁-C₆)aminoalkyl radical inwhich the alkyl is unsubstituted or substituted with one or morehydroxyl radicals; a (C₁-C₆)aminoalkyl radical in which the alkyl isunsubstituted or substituted with one or more hydroxyl radicals and inwhich the amine is substituted with one or two radicals, which may beidentical or different, chosen from alkyl, (C₁-C₆)monohydroxyalkyl,(C₂-C₆)polyhydroxyalkyl, (C₁-C₆)alkylcarbonyl, carbamyl,N—(C₁-C₆)alkylcarbamyl, N,N-di(C₁-C₆)alkylcarbamyl, C₁-C₆alkylsulphonyl, formyl, trifluoro(C₁-C₆)-alkylcarbonyl,(C₁-C₆)alkylcarboxyl and thiocarbamyl radicals, or from a group Z asdefined below, or which may form, together with the nitrogen atom towhich they are attached, a 5- or 6-membered ring which is carbon basedor which contains one or more hetero atoms; R₆ is chosen from a(C₁-C₆)alkyl radical; a (C₁-C₆)monohydroxyalkyl radical; a(C₂-C₆)polyhydroxyalkyl radical; a group Z as defined below; a(C₁-C₆)alkoxy(C₁-C₆)alkyl radical; an aryl radical; a benzyl radical; acarboxy(C₁-C₆)alkyl radical; a (C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radical;a cyano(C₁-C₆)alkyl radical; a carbamyl(C₁-C₆)alkyl radical; anN—(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radical; anN,N-di(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radical; a (C₁-C₆)trifluoroalkylradical; a (C₁-C₆)aminosulphonylalkyl radical; a(C₁-C₆)N—Z-aminosulphonylalkyl radical, anN—(C₁-C₆)alkylaminosulphonyl(C₁-C₆)alkyl radical; an N₃,N-di(C₁-C₆)alkylaminosulphonyl(C₁-C₆)alkyl radical; a(C₁-C₆)alkylsulphinyl (C₁-C₆)alkyl radical; a(C₁-C₆)alkylsulphonyl(C₁-C₆)alkyl radical; a (C_(1-C) ₆)alkylcarbonyl(C₁-C₆)alkyl radical; a (C₁-C₆)aminoalkyl radical in which the alkyl isunsubstituted or substituted with one or more hydroxyl radicals; and a(C₁-C₆)aminoalkyl radical in which the alkyl is unsubstituted orsubstituted with one or more hydroxyl radicals and in which the amine issubstituted with one or two identical or different radicals chosen from(C₁-C₆)alkyl, (C₁-C₆)monohydroxyalkyl, (C₂-C₆)polyhydroxyalkyl,(C₁-C₆)alkylcarbonyl, formyl, trifluoro(C₁-C₆)alkylcarbonyl,(C₁-C₆)alkylcarboxyl, carbamyl, N—(C₁-C₆)alkylcarbamyl,N,N-di(C₁-C₆)alkylcarbamyl, thiocarbamyl and (C₁-C₆)alkylsulphonylradicals, or from a group Z as defined below; or which may form,together with the nitrogen atom to which they are attached, a 5- or6-membered ring which is carbon-based or which contains one or morehetero atoms; R₄, R₅, R₇ and R₈, which may be identical or different,are chosen from a hydrogen atom; a group Z as defined below, in whichthe linker arm D contains no ketone functions directly linked to thenitrogen atom bearing the radicals R₄ and R₅; a (C₁-C₆)alkyl radical; a(C₁-C₆)monohydroxyalkyl radical; a (C₂-C₆)polyhydroxyalkyl radical; a(C₁-C₆)alkoxy(C₁-C₆)alkyl radical; an aryl radical; a benzyl radical; acyano(C₁-C₆)alkyl radical; a carbamyl(C₁-C₆)alkyl radical; anN—(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radical; anN,N-di(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radical; athiocarbamyl(C₁-C₆)alkyl radical; a (C₁-C₆)trifluoroalkyl radical; a(C₁-C₆)sulphoalkyl radical; a (C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radical; a(C₁-C₆)alkylsulphinyl(C₁-C₆)alkyl radical; a (C₁-C₆)aminosulphonylalkylradical; a (C₁-C₆)N—Z-aminosulphonylalkyl radical; anN—(C₁-C₆)alkylaminosulphonyl(C₁-C₆)alkyl radical; anN,N-di(C₁-C₆)alkylaminosulphonyl(C₁-C₆)alkyl radical; a(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radical; a (C₁-C₆)aminoalkyl radical inwhich the alkyl is unsubstituted or substituted with one or morehydroxyl radicals; and a (C₁-C₆)aminoalkyl radical in which the alkyl isunsubstituted or substituted with one or more hydroxyl radicals and inwhich the amine is substituted with one or two identical or differentradicals chosen from (C₁-C₆)alkyl, (C₁-C₆)monohydroxyalkyl,(C₂-C₆)polyhydroxyalkyl, (C₁-C₆)alkylcarbonyl, carbamyl,N—(C₁-C₆)alkylcarbamyl, N,N-di(C₁-C₆)alkylcarbamyl,(C₁-C₆)alkylsulphonyl, formyl, trifluoro(C₁-C₆)alkylcarbonyl,(C₁-C₆)alkylcarboxyl and thiocarbamyl radicals, or from a group Z asdefined below; or which may form, together with the nitrogen atom towhich they are attached, a 5- or 6-membered ring which is carbon-basedor which contains one or more hetero atoms; Z is chosen from theunsaturated cationic groups of formulae (II) and (III) below, and thesaturated cationic groups of formula (IV) below:

in which: D is a linker arm which represents a linear or branched alkylchain, which can be interrupted by one or more hetero atoms, and whichcan be substituted with one or more hydroxyl or C₁-C₆ alkoxy radicals,and which can bear one or more ketone functions; the ring members E, G,J, L and M, which may be identical or different, are chosen from acarbon, oxygen, sulphur and nitrogen; n is an integer ranging from 0 to4; m is an integer ranging from 0 to 5; the R radical, which may beidentical or different, are chosen from a second Z group, which isidentical to or different from the first Z group, a halogen atom, ahydroxyl radical, a (C₁-C₆)alkyl radical, a (C₁-C₆)monohydroxyalkylradical, a (C₂-C₆)polyhydroxyalkyl radical, a nitro radical, a cyanoradical, a cyano(C₁-C₆)alkyl radical, a (C₁-C₆)alkoxy radical, atri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radical, an amido radical, a formylradical, a carboxyl radical, a (C₁-C₆)alkylcarbonyl radical, a thioradical, a (C₁-C₆)thioalkyl radical, a (C₁-C₆)alkylthio radical, anamino radical, an amino radical protected with a (C₁-C₆)alkylcarbonyl,carbamyl or (C₁-C₆)alkylsulphonyl radical; a group NHRO or NROR″ inwhich RO and R″, which may be identical or different, are chosen from a(C₁-C₆)alkyl radical, a (C₁-C₆)monohydroxyalkyl radical and a(C₂-C₆)polyhydroxyalkyl radical; R₉ is chosen from a (C₁-C₆)alkylradical, a (C₁-C₆)monohydroxyalkyl radical, a (C₂-C₆)polyhydroxyalkylradical, a cyano(C₁-C₆)alkyl radical, atri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radical, a (C₁-C₆)alkoxy(C₁-C₆)alkylradical, a carbamyl-(C₁-C₆)alkyl radical, a(C₁-C₆)alkylcarboxy(C₁-C₆)-alkyl radical, a benzyl radical and a secondZ group, which is identical to or different from the first Z group; R₁₀,R₁₁ and R₁₂, which may be identical or different, are chosen from a(C₁-C₆)alkyl radical, a (C₁-C₆)monohydroxyalkyl radical, a(C₂C₆)polyhydroxyalkyl radical, a (C₁-C₆)alkoxy(C₁-C₆)alkyl radical, acyano(C₁-C₆)alkyl radical, an aryl radical, a benzyl radical, a(C₁-C₆)amidoalkyl radical, a tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicaland a (C₁-C₆)aminoalkyl radical in which the amine is protected by a(C₁-C₆)alkylcarbonyl, carbamyl or (C₁-C₆)alkylsulphonyl radical; two ofthe R₁₀, R₁₁ and R₁₂ radicals may also together form, with the nitrogenatom to which they are attached, a carbonaceous saturated 5- or6-membered ring or which contains one or more hetero atoms, wherein saidring may be unsubstituted or substituted with a halogen atom, a hydroxylradical, a (C₁-C₆)alkyl radical, a (C₁-C₆)monohydroxyalkyl radical, a(C₂C₆)polyhydroxyalkyl radical, a nitro radical, a cyano radical, acyano(C₁-C₆)alkyl radical, a (C₁-C₆)alkoxy radical, atri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radical, an amido radical, a formylradical, a carboxyl radical, a keto(C₁-C₆)alkyl radical, a thio radical,a (C₁-C₆)thioalkyl radical, a (C₁-C₆)alkylthio radical, an amino radicalor an amino radical protected with a (C₁-C₆)alkylcarbonyl, carbamyl or(C₁-C₆)alkylsulphonyl radical; one of the R₁₀, R₁₁, and R₁₂ radicals mayalso be chosen from a second Z group which is identical to or differentfrom the first Z group; R₁₃ is chosen from a (C₁-C₆)alkyl radical; a(C₁-C₆)monohydroxy-alkyl radical; a (C₂-C₆)polyhydroxyalkyl radical; anaryl radical; a benzyl radical; a (C₁-C₆)aminoalkyl radical, a(C₁-C₆)aminoalkyl radical in which the amine is protected by a(C₁-C₆)alkylcarbonyl, carbamyl or (C₁-C₆)alkylsulphonyl radical; acarboxy(C₁-C₆)alkyl radical; a cyano(C₁-C₆)alkyl radical; acarbamyl(C₁-C₆)alkyl radical; a (C₁-C₆)trifluoroalkyl radical; atri(C₁-C₆)alkylsilane-(C₁-C₆)alkyl radical; a (C₁-C₆)sulphonamidoalkylradical; a (C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radical; a(C₁-C₆)alkylsulphinyl(C₁-C₆)alkyl radical; a(C₁-C₆)alkylsulphonyl(C₁-C₆)alkyl radical; a(C₁-C₆)alkylketo(C₁-C₆)alkyl radical, anN—(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radical; and anN—(C₁-C₆)alkylsulphonamido(C₁-C₆)alkyl radical; a and y are integersequal to 0 or 1; with the following conditions: in the unsaturatedcationic groups of formula (II): when a=0, the linker arm D is attachedto the nitrogen atom, when a=1, the linker arm D is attached to one ofthe ring members E, G, J or L, y can take the value 1 only: 1) when thering members E, G, J and L simultaneously represent a carbon atom andwhen the R₉ radical is carried by the nitrogen atom of the unsaturatedring; or alternatively 2) when at least one of the ring members E, G, Jand L represents a nitrogen atom to which the Rs radical is attached; inthe unsaturated cationic groups of formula (III): when a=0, the linkerarm D is attached to the nitrogen atom, when a=1, the linker arm D isattached to one of the ring members E, G, J, L or M, y can take thevalue 1 only when at least one of the ring members E, G, J, L and Mrepresents a divalent atom and when the R₉ radical is carried by thenitrogen atom of the unsaturated ring; in the cationic groups of formula(IV): when a=0, then the linker arm D is attached to the nitrogen atomcarrying the R₁₀ to R₁₂ radicals, when a=1, then two of the R₁₀ to R₁₂radicals form, together with the nitrogen atom to which they areattached, a saturated 5- or 6-membered ring as defined above, and thelinker arm D is carried by a carbon atom of the saturated ring; X⁻ is amonovalent or divalent anion; with the proviso that the number ofcationic Z groups in the compound of formula (I) is at least equal to 1.11. The composition according to claim 10, wherein said at least onecompound of formula (I) is present in said composition in an amountranging from 0.0005 to 12% by weight relative to the total weight of thecomposition.
 12. The composition according to claim 11, wherein said atleast one compound of formula (I) is present in said composition in anamount ranging from 0.005 to 6% by weight relative to the total weightof the composition.
 13. The composition according to claim 10, furthercomprising at least one oxidation base chosen frompara-phenylenediamines, bis(phenyl)alkylenediamines, para-aminophenols,ortho-aminophenols and heterocyclic bases.
 14. The composition accordingto claim 13, wherein the heterocyclic bases are chosen from pyridinederivatives, pyrimidine derivatives and pyrazole derivatives.
 15. Thecomposition according to claim 13, wherein said at least one oxidationbase is present in said composition in an amount ranging from 0.0005 to12% by weight relative to the total weight of the composition.
 16. Thecomposition according to claim 10, further comprising at least onecoupler chosen from meta-phenylenediamines, meta-aminophenols,meta-diphenols and heterocyclic couplers, and/or at least one directdye.
 17. The composition according to claim 16, wherein said at leastone coupler is chosen from 2-methyl-5-aminophenol, 5-N-(β-hydroxyethyl)amino-2-methylphenol, 3-aminophenol, 1,3-dihydroxybenzene,1,3-dihydroxy-2-methylbenzene, 4-chloro-1,3-dihydroxybenzene,2,4-diamino-1-(β-hydroxyethyloxy)benzene,2-amino-4-(β-hydroxyethylamino)-1-methoxybenzene, 1,3-diaminobenzene,1,3-bis(2,4-diaminophenoxy)propane, sesamol, α-naphthol,6-hydroxyindole, 4-hydroxyindole, 4-hydroxy-N-methylindole,6-hydroxyindoline, 2,6-dihydroxy-4-methylpyridine,1H-3-methylpyrazol-5-one, 1-phenyl-3-methylpyrazol-5-one and3,6-dimethylpyrazolo(3,2-c)-1,2,4-triazole, and acid addition saltsthereof.
 18. The composition according to claim 16, wherein said atleast one coupler is present in said composition in an amount rangingfrom 0.0001 to 10% by weight relative to the total weight of thecomposition.
 19. The composition according to claim 10, wherein the acidaddition salts are chosen from hydrochlorides, hydrobromides, sulphates,citrates, succinates, tartrates, lactates and acetates.
 20. Thecomposition according to claim 10, wherein said keratin fibers are humankeratin fibers.
 21. The composition according to claim 10, wherein saidhuman keratin fibers are hair.
 22. The composition according to claim10, wherein in at least one of said formulae (II), (III), and (IV), D isa linear or branched alkyl chain containing from 1 to 14 carbon atoms.23. The composition according to claim 10, wherein in at least one ofsaid formulae (II), (III), and (IV), D can be interrupted by oxygen,sulphur, or nitrogen atoms.
 24. A process for the oxidation-dyeing ofkeratin fibers comprising applying to said keratin fibers for a periodwhich is sufficient to develop the desired coloration, at least one dyecomposition comprising, in a medium suitable for dyeing, at least onecompound of formula (I) below, or an acid addition salt thereof whereinsaid developing is carried out either in air or in the presence of anoxidizing agent:

in which; A₁, A₂ and A₃, which may be identical or different, are chosenfrom a group —NR₇R₈ and a hydroxyl radical; one and only one of thegroups A₁, A₂ and A₃ may also represent a group R₃ as defined below; R₁R₂ and R₃, which may be identical or different, are chosen from ahydrogen atom; a halogen atom; a group Z as defined below; a(C₁-C₆)alkylcarbonyl radical; an amino(C₁-C₆)alkylcarbonyl radical; anN—Z-amino(C₁-C₆)alkylcarbonyl radical; anN—(C₁-C₆)alkylamino(C₁-C₆)alkylcarbonyl radical; anN,N-di(C₁-C₆)-alkylamino(C₁-C₆)alkylcarbonyl radical; anamino(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radical; anN—Z-amino(C₁C₆)alkylcarbonyl(C₁-C₆)alkyl radical; anN—(C₁-C₆)alkyl-amino(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radical; anN,N-di(C₁-C₆)alkylamino(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radical; acarboxyl radical; a (C₁-C₆)alkylcarboxyl radical; a(C₁-C₆)alkylsulphonyl radical; an aminosulphonyl radical; anN—Z-aminosulphonyl radical; a (C₁-C₆)N-alkylaminosulphonyl radical; anN,N-di(C₁-C₆)alkylaminosulphonyl radical; a (C₁ -C₆)aminosulphonylalkylradical; a (C₁-C₆)N—Z-aminosulphonylalkyl radical; anN—(C₁-C₆)alkylaminosulphonyl(C₁-C₆)alkyl radical; anN,N-di(C₁-C₆)-alkylaminosulphonyl(C₁-C₆)alkyl radical; a carbamylradical; an N—(C₁-C₆)alkycarbamyl radical; an N,N-di(C₁-C₆)alkylcarbamylradical; a carbamyl(C₁-C₆)alkyl radical; anN—(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radical; anN,N-di(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radical; a (C₁-C₆)alkyl radical:a (C₁-C₆)monohydroxyalkyl radical; a (C₁-C₆)polyhydroxyalkyl radical; a(C₁-C₆)alkoxy(C₁-C₆)alkyl radical; a (C₁-C₆)trifluoroalkyl radical; acyano radical; a group OR₆ or SR₆; an amino group protected by a(C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylcarboxyl,trifluoro(C₁-C₆)alkylcarbonyl, amino(C₁-C₆)alkylcarbonyl,N—Z-amino(C₁-C₆)alkylcarbonyl, N—(C₁-C₆)alkylamino(C₁-C₆)alkylcarbonyl,N,N-di(C₁-C₆)alkylamino(C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylcarboxyl,carbamyl, N—(C₁-C₆)alkylcarbamyl, N,N-di(C₁-C₆)alkylcarbamyl,(C₁-C₆)alkylsulphonyl, aminosulphonyl, N—Z-aminosulphonyl,(C₁-C₆)N-alkylaminosulphonyl, N,N-di(C₁-C₆)alkylaminosulphonyl,thiocarbamyl or formyl radical, or with a group Z as defined below inwhich a linker arm D comprises a ketone function directly attached tothe nitrogen atom of the amino group; and a (C₁-C₆)aminoalkyl radical inwhich the alkyl is unsubstituted or substituted with one or morehydroxyl radicals; a (C₁-C₆)aminoalkyl radical in which the alkyl isunsubstituted or substituted with one or more hydroxyl radicals and inwhich the amine is substituted with one or two radicals, which may beidentical or different, chosen from alkyl, (C₁-C₆)monohydroxyalkyl,(C₁-C₆)polyhydroxyalkyl, (C₁-C₆)alkylcarbonyl, carbamyl,N—(C₁-C₆)alkylcarbamyl, N,N-di(C₁-C₆)alkylcarbamyl, C₁-C₆alkylsulphonyl, formyl, trifluoro (C₁-C₆)-alkylcarbonyl,(C₁-C₆)alkylcarboxyl and thiocarbamyl radicals, or from a group Z asdefined below, or which may form, together with the nitrogen atom towhich they are attached, a 5- or 6-membered ring which is carbon-basedor which contains one or more hetero atoms; R₆ is chosen from a(C₁-C₆)alkyl radical; a (C₁-C₆)monohydroxyalkyl radical; a(C₂-C₆)polyhydroxyalkyl radical; a group Z as defined below; a(C₁-C₆)alkoxy(C₁-C₆)alkyl radical; an aryl radical; a benzyl radical; acarboxy(C₁-C₆)alkyl radical; a (C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radical;a cyano(C₁-C₆)alkyl radical; a carbamyl(C₁-C₆)alkyl radical; anN—(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radical; anN,N-di(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radical; a (C₁-C₆)trifluoroalkylradical; a (C₁-C₆)aminosulphonylalkyl radical; a(C₁-C₆)N—Z-aminosulphonylalkyl radical; anN—(C₁-C₆)alkylaminosulphonyl(C₁-C₆)alkyl radical; anN,N-di(C₁-C₆)alkylaminosulphonyl(C₁-C₆)alkyl radical; a(C₁-C₆)alkylsulphinyl (C₁-C₆)alkyl radical; a (C₁-C₆)alkylsulphonyl(C₁-C₆)alkyl radical; a (C₁-C₆)alkylcarbonyl (C₁-C₆)alkyl radical; a(C₁-C₆)aminoalkyl radical in which the alkyl is unsubstituted orsubstituted with one or more hydroxyl radicals; and a (C₁-C₆)aminoalkylradical in which the alkyl is unsubstituted or substituted with one ormore hydroxyl radicals and in which the amine is substituted with one ortwo identical or different radicals chosen from (C₁-C₆)alkyl,(C₁-C₆)monohydroxyalkyl, (C₂-C₆)polyhydroxyalkyl, (C₁-C₆)alkylcarbonyl,formyl, trifluoro(C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylcarboxyl, carbamyl,N—(C₁-C₆)alkylcarbamyl, N,N-di(C₁-C₆)alkylcarbamyl, thiocarbamyl and(C₁-C₆)alkylsulphonyl radicals, or from a group Z as defined below; orwhich may form, together with the nitrogen atom to which they areattached, a 5- or 6-membered ring which is carbon-based or whichcontains one or more hetero atoms; R₄, R₅, R₇ and R₈, which may beidentical or different, are chosen from a hydrogen atom; a group Z asdefined below, in which the linker arm D contains no ketone functionsdirectly linked to the nitrogen atom bearing the radicals R₄ and R₅; a(C₁-C₆)alkyl radical; a (C₁-C₆)monohydroxyalkyl radical; a(C₂-C₆)polyhydroxyalkyl radical, a (C₁-C₆)alkoxy(C,₁-C₆)alkyl radical;an aryl radical; a benzyl radical; a cyano(C₁-C₆)alkyl radical; acarbamyl(C₁-C₆)alkyl radical; an N—(C₁-C₆)alkylcarbamyl(C₁-C₆)alkylradical; an N,N-di(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radical; athiocarbamyl(C₁-C₆)alkyl radical; a (C₁-C₆)trifluoroalkyl radical; a(C₁-C₆)sulphoalkyl radical; a (C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radical; a(C₁-C₆)alkylsulphinyl(C₁-C₆)alkyl radical; a (C₁-C₆)aminosulphonylalkylradical; a (C₁-C₆)N—Z-aminosulphonylalkyl radical; anN—(C₁-C₆)alkylaminosulphonyl(C₁-C₆)alkyl radical; anN,N-di(C₁-C₆)alkylaminosulphonyl(C₁-C₆)alkyl radical; a(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radical; a (C₁-C₆)aminoalkyl radical inwhich the alkyl is unsubstituted or substituted with one or morehydroxyl radicals; and a (C₁-C₆)aminoalkyl radical in which the alkyl isunsubstituted or substituted with one or more hydroxyl radicals and inwhich the amine is substituted with one or two identical or differentradicals chosen from (C₁-C₆)alkyl, (C₁-C₆)monohydroxyalkyl,(C₂-C₆)polyhydroxyalkyl, (C₁-C₆)alkylcarbonyl, carbamyl,N—(C₁-C₆)alkylcarbamyl, N,N-di(C₁-C₆)alkylcarbamyl,(C₁-C₆)alkylsulphonyl, formyl, trifluoro(C₁-C₆)alkylcarbonyl,(C₁-C₆)alkylcarboxyl and thiocarbamyl radicals, or from a group Z asdefined below; or which may form, together with the nitrogen atom towhich they are attached, a 5- or 6-membered ring which is carbon-basedor which contains one or more hetero atoms; Z is chosen from theunsaturated cationic groups of formulae (II) and (III) below, and thesaturated cationic groups of formula (IV) below:

in which: D is a linker arm which represents a linear or branched alkylchain, which can be interrupted by one or more hetero atoms, and whichcan be substituted with one or more hydroxyl or C₁-C₆ alkoxy radicals,and which can bear one or more ketone functions; the ring members E, G,J, L and M, which may be identical or different, are chosen from acarbon, oxygen, sulphur and nitrogen; n is an integer ranging from 0 to4; m is an integer ranging from 0 to 5; the R radical, which may beidentical or different, are chosen from a second Z group, which isidentical to or different from the first Z group, a halogen atom, ahydroxyl radical, a (C₁-C₆)alkyl radical, a (C₁-C₆)monohydroxyalkylradical, a (C₂-C₆)polyhydroxyalkyl radical, a nitro radical, a cyanoradical, a cyano(C₁-C₆)alkyl radical, a (C₁-C₆)alkoxy radical, atri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radical, an amido radical, a formylradical, a carboxyl radical, a (C₁-C₆)alkylcarbonyl radical, a thioradical, a (C₁-C₆)thioalkyl radical, a (C₁-C₆)alkylthio radical, anamino radical, an amino radical protected with a (C₁-C₆)alkylcarbonyl,carbamyl or (C₁-C₆)alkylsulphonyl radical; a group NHRO or NROR″ inwhich RO and R″, which may be identical or different, are chosen from a(C₁-C₆)alkyl radical, a (C₁-C₆,)monohydroxyalkyl radical and a(C₂-C₆)polyhydroxyalkyl radical; R₉ is chosen from a (C₁-C₆)alkylradical, a (C₁-C₆)monohydroxyalkyl radical, a (C₂-C₆)polyhydroxyalkylradical, a cyano(C₁-C₆)alkyl radical, atri(C₁-C₆,)alkylsilane(C₁-C₆)alkyl radical, a (C₁-C₆)alkoxy(C₁-C₆)alkylradical, a carbamyl-(C₁-C₆)alkyl radical, a(C₁-C₆)alkylcarboxy(C₁-C₆)-alkyl radical, a benzyl radical and a secondZ group, which is identical to or different from the first Z group; R₁₀R₁₁ and R₁₂, which may be identical or different, are chosen from a(C₁-C₆)alkyl radical, a (C₁-C₆)monohydroxyalkyl radical, a(C₁-C₆)polyhydroxyalkyl radical, a (C₁-C₆)alkoxy(C₁-C₆)alkyl radical, acyano(C₁-C₆)alkyl radical, an aryl radical, a benzyl radical, a(C₁-C₆)amidoalkyl radical, a tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicaland a (C₁-C₆)aminoalkyl radical in which the amine is protected by a(C₁-C₆)alkylcarbonyl, carbamyl or (C₁-C₆)alkylsulphonyl radical; two ofthe R₁₀, R₁₁, and R₁₂ radicals may also together form, with the nitrogenatom to which they are attached, a carbonaceous saturated 5- or6-membered ring or which contains one or more hetero atoms, wherein saidring may be unsubstituted or substituted with a halogen atom, a hydroxylradical, a (C₁-C₆)alkyl radical, a (C₁-C₆)monohydroxyalkyl radical, a(C₂-C₆)polyhydroxyalkyl radical, a nitro radical, a cyano radical, acyano(C₁-C₆)alkyl radical, a (C₁-C₆)alkoxy radical, atri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radical, an amido radical, a formylradical, a carboxyl radical, a keto(C₁-C₆)alkyl radical, a thio radical,a (C₁-C₆)thioalkyl radical, a (C₁-C₆)alkylthio radical, an amino radicalor an amino radical protected with a (C₁-C₆)alkylcarbonyl, carbamyl or(C₁-C₆)alkylsulphonyl radical; one of the R₁₀, R₁₁, and R₁₂ radicals mayalso be chosen from a second Z group which is identical to or differentfrom the first Z group; R₁₃ is chosen from a (C₁-C₆)alkyl radical; a(C₁-C₆)monohydroxy-alkyl radical; a (C₂-C₆)polyhydroxyalkyl radical; anaryl radical; a benzyl radical; a (C₁-C₆)aminoalkyl radical, a(C₁-C₆)aminoalkyl radical in which the amine is protected by a(C₁-C₆)alkylcarbonyl, carbamyl or (C₁-C₆)alkylsulphonyl radical; acarboxy(C₁-C₆)alkyl radical; a cyano(C₁-C₆)alkyl radical; acarbamyl(C₁-C₆)alkyl radical; a (C₁-C₆)trifluoroalkyl radical; atri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radical; a (C₁-C₆)sulphonamidoalkylradical; a (C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radical; a(C₁-C₆)alkylsulphinyl(C₁-C₆)alkyl radical; a(C₁-C₆)alkylsulphonyl(C₁-C₆)alkyl radical; a(C₁-C₆)alkylketo(C₁-C₆)alkyl radical; anN—(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radical; and anN—(C₁-C₆)alkylsulphonamido(C₁-C₆)alkyl radical; a and y are integersequal to 0 or 1; with the following conditions: in the unsaturatedcationic groups of formula (II): when a=0, the linker arm D is attachedto the nitrogen atom, when a=1, the linker arm D is attached to one ofthe ring members E, G, J or L, y can take the value 1 only: 1) when thering members E, G, J and L simultaneously represent a carbon atom andwhen the R₉ radical is carried by the nitrogen atom of the unsaturatedring; or alternatively 2) when at least one of the ring members E, G, Jand L represents a nitrogen atom to which the R₉ radical is attached; inthe unsaturated cationic groups of formula (III): when a=0, the linkerarm D is attached to the nitrogen atom, when a=1, the linker arm D isattached to one of the ring members E, G, J, L or M, y can take thevalue 1 only when at least one of the ring members E, G, J, L and Mrepresents a divalent atom and when the R₉ radical is carried by thenitrogen atom of the unsaturated ring; in the cationic groups of formula(IV): when a=0, then the linker arm D is attached to the nitrogen atomcarrying the R₁₀ to R₁₂ radicals, when a=1, then two of the R₁₀ to R₁₂radicals form, together with the nitrogen atom to which they areattached, a saturated 5- or 6-membered ring as defined above, and thelinker arm D is carried by a carbon atom of the saturated ring; X⁻ is amonovalent or divalent anion; with the proviso that the number ofcationic Z groups in the compound of formula (I) is at least equal to 1.25. The process according to claim 24, wherein in at least one of saidformulae (II), (III), and (IV), D is a linear or branched alkyl chaincontaining from 1 to 14 carbon atoms.
 26. The process according to claim24, wherein in at least one of said formulae (II), (III), and (IV), Dcan be interrupted by oxygen, sulphur, or nitrogen atoms.
 27. Theprocess according to claim 24, wherein the coloration of the fibers canbe carried out without the addition of an oxidizing agent, merely oncontact with atmospheric oxygen.
 28. The process according to claim 24,wherein color is developed at acidic, neutral or alkaline pH using anoxidizing agent which is added to the dye composition at the time ofapplication, or which is present in an oxidizing composition that isapplied simultaneously or sequentially in a separate manner.
 29. Theprocess according to claim 24, wherein the oxidizing agent is chosenfrom hydrogen peroxide, urea peroxide, alkali metal bromates, persaltsand enzymes.
 30. The process according to claim 29, wherein the enzymesare chosen from peroxidases, laccases, tyrosinases and oxidoreductases.31. The process according to claim 30, wherein the oxidoreductases arechosen from pyranose oxidases, glucose oxidases, glycerol oxidases,lactate oxidases, pyruvate oxidases and uricases.
 32. The processaccording to claim 24, wherein the keratin fibers are human keratinfibers.
 33. The process according to claim 24, wherein the human keratinfibers are hair.
 34. A multi-compartment dyeing device comprising afirst compartment and a second compartment, wherein said firstcompartment contains a dye composition comprising at least one dyecomposition comprising at least one compound of formula (I) below, or anacid addition salt thereof:

in which: A₁, A₂ and A₃, which may he identical or different, are chosenfrom a group —NR₇R₈ and a hydroxyl radical; one and only one of thegroups A₁, A₂ and A₃ may also represent a group R₃ as defined below; R₁,R₂ and R₃, which may be identical or different, are chosen from ahydrogen atom; a halogen atom; a group Z as defined below; a(C₁-C₆)alkylcarbonyl radical; an amino(C₁-C₆)alkylcarbonyl radical; anN—Z-amino(C₁-C)alkylcarbonyl radical, anN—(C₁-C₆)alkylamino(C₁-C₆)alkylcarbonyl radical; anN,N-di(C₁-C₆)-alkylamino(C₁-C₆)alkylcarbonyl radical; anamino(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radical; anN—Z-amino(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radical; anN(C₁-C₆)alkyl-amino(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radical; anN,N-di(C₁-C₆)alkylamino(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radical; acarboxyl radical; a (C₁-C₆)alkylcarboxyl radical; a(C₁-C₆)alkylsulphonyl radical; an aminosulphonyl radical; anN—Z-aminosulphonyl radical; a (C₁-C₆)N-alkylaminosulphonyl radical; anN,N-di(C₁-C₆)alkylaminosulphonyl radical; a (C₁-C₆)aminosulphonylalkylradical; a (C₁-C₆)N—Z-aminosulphonylalkyl radical; anN—(C₁-C₆)alkylaminosulphonyl(C₁-C₆)alkyl radical; anN,N-di(C₁-C₆)-alkylaminosulphonyl(C₁-C₆)alkyl radical; a carbamylradical; an N—(C₁-C₆)alkylcarbamyl radical; anN,N-di(C₁-C₆)alkylcarbamyl radical; a carbamyl(C₁-C₆)alkyl radical; anN—(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radical; anN,N-di(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radical; a (C₁-C₆)alkyl radical;a (C₁-C₆)monohydroxyalkyl radical; a (C₂-C₆)polyhydroxyalkyl radical; a(C₁-C₆)alkoxy(C₁-C₆)alkyl radical; a (C₁-C₆)trifluoroalkyl radical; acyano radical; a group OR₆ or SR₆; an amino group protected by a(C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylcarboxyl,trifluoro(C₁-C₆)alkylcarbonyl, amino(C₁-C₆)alkylcarbonyl,N—Z-amino(C₁-C₆)alkylcarbonyl, N-(C₁-C₆)alkylamino(C₁-C₆)alkylcarbonyl,N,N-di(C₁-C₆)alkylamino(C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylcarboxyl,carbamyl, N—(C₁-C₆)alkylcarbamyl, N,N-di(C₁-C₆)alkylcarbamyl,(C₁-C₆)alkylsulphonyl, aminosulphonyl, N—Z-aminosulphonyl,(C₁-C₆)N-alkylaminosulphonyl, N,N-di(C₁-C₆)alkylaminosulphonyl,thiocarbamyl or formyl radical, or with a group Z as defined below inwhich a linker arm D comprises a ketone function directly attached tothe nitrogen atom of the amino group; and a (C₁-C₆)aminoalkyl radical inwhich the alkyl is unsubstituted or substituted with one or morehydroxyl radicals; a (C₁-C₆)aminoalkyl radical in which the alkyl isunsubstituted or substituted with one or more hydroxyl radicals and inwhich the amine is substituted with one or two radicals, which may beidentical or different, chosen from alkyl, (C₁-C₆)monohydroxyalkyl,(C₂-C₆)polyhydroxyalkyl, (C₁-C₆)alkylcarbonyl, carbamyl,N—(C₁-C₆)alkylcarbamyl, N,N-di(C₁l₆)alkylcarbamyl, C₁-C₆ alkylsulphonyl,formyl, trifluoro(C₁-C₆)-alkylcarbonyl, (C₁-C₆)alkylcarboxyl andthiocarbamyl radicals, or from a group Z as defined below, or which mayform, together with the nitrogen atom to which they are attached, a 5-or 6-membered ring which is carbon-based or which contains one or morehetero atoms; R₆ is chosen from a (C₁-C₆)alkyl radical; a(C₁-C₆)monohydroxyalkyl radical; a (C₂C₆)polyhydroxyalkyl radical; agroup Z as defined below; a (C₁-C₆)alkoxy(C₁-C₆)alkyl radical; an arylradical; a benzyl radical; a carboxy(C₁-C₆)alkyl radical; a(C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radical; a cyano(C₁-C₆)alkyl radical; acarbamyl(C₁-C₆)alkyl radical; an N—(C₁-C₆)alkylcarbamyl(C₁-C₆)alkylradical; an N,N-di(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radical; a(C₁-C₆)trifluoroalkyl radical; a (C₁-C₆)aminosulphonylalkyl radical; a(C₁-C₆)N—Z-aminosulphonylalkyl radical; anN—(C₁-C₆)alkylaminosulphonyl(C₁-C₆)alkyl radical; anN,N-di(C₁-C₆)alkylaminosulphonyl(C₁-C₆)alkyl radical; a(C₁-C₆)alkylsulphinyl (C₁-C₆ alkyl radical; a (C₁-C₆)alkylsulphonyl(C₁-C₆)alkyl radical; a (C₁-C₆)alkylcarbonyl (C₁-C₆)alkyl radical; a(C₁-C₆)aminoalkyl radical in which the alkyl is unsubstituted orsubstituted with one or more hydroxyl radicals; and a (C₁-C₆)aminoalkylradical in which the alkyl is unsubstituted or substituted with one ormore hydroxyl radicals and in which the amine is substituted with one ortwo identical or different radicals chosen from (C₁-C₆)alkyl,(C₁-C₆)monohydroxyalkyl, (C₂-C₆)polyhydroxyalkyl, (C₁-C₆)alkylcarbonyl,formyl, trifluoro(C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylcarboxyl, carbamyl,N—(C₁-C₆)alkylcarbamyl, N,N-di(C₁-C₆)alkylcarbamyl, thiocarbamyl and(C₁-C₆)alkylsulphonyl radicals, or from a group Z as defined below; orwhich may form, together with the nitrogen atom to which they areattached, a 5- or 6-membered ring which is carbon-based or whichcontains one or more hetero R₄, R₅, R₇ and R₈, which may be identical ordifferent are chosen from a hydrogen atom; a group Z as defined below,in which the linker arm D contains no ketone functions directly linkedto the nitrogen atom bearing the radicals R₄ and R₅; a (C₁-C₆)alkylradical; a (C₁-C₆)monohydroxyalkyl radical; a (C₂-C₆)polyhydroxyalkylradical; a (C₁Gr)alkoxy(C₁-C₆)alkyl radical; an aryl radical; a benzylradical; a cyano(C₁-C₆)alkyl radical; a carbamyl(C₁-C₆)alkyl radical; anN—(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radical; anN,N-di(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radical; athiocarbamyl(C₁-C₆)alkyl radical; a (C₁-C₆)trifluoroalkyl radical; a(C₁-C₆)sulphoalkyl radical; a (C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radical: a(C₁-C₆)alkylsulphinyl(C₁-C₆)alkyl radical; a (C₁-C₆)aminosulphonylalkylradical; a (C₁-C₆)N—Z-aminosulphonylalkyl radical; anN—(C₁C₆)alkylaminosulphonyl(C₁-C₆)alkyl radical; anN,N-di(C₁-C₆)alkylaminosulphonyl(C₁-C₆)alkyl radical; a(C₁-C)alkylcarbonyl(C₁-C₆)alkyl radical; a (C₁-C₆)aminoalkyl radical inwhich the alkyl is unsubstituted or substituted with one or morehydroxyl radicals; and a (C₁-C₆)aminoalkyl radical in which the alkyl isunsubstituted or substituted with one or more hydroxl radicals and inwhich the amine is substituted with one or two identical or differentradicals chosen from (C₁-C₆)alkyl, (C₁-C₆)monohydroxyalkyl,(C₂-C₆)polyhydroxyalkyl, (C₁-C₆)alkylcarbonyl, carbamyl,N—(C₁-C₆)alkylcarbamyl, N,N-di(C₁-C₆)alkylcarbamyl,(C₁-C₆)alkylsulphonyl, formyl, trifluoro(C₁-C₆)alkylcarbonyl,(C₁-C₆)alkylcarboxyl and thiocarbamyl radicals, or from a group Z asdefined below; or which may form, together with the nitrogen atom towhich they are attached, a 5- or 6-membered ring which is carbon-basedor which contains one or more hetero atoms; Z is chosen from theunsaturated cationic groups of formulae (II) and (III) below, and thesaturated cationic groups of formula (IV) below:

in which: D is a linker arm which represents a linear or branched alkylchain, which can be interrupted by one or more hetero atoms, and whichcan be substituted with one or more hydroxyl or C₁-C₆ alkoxy radicals,and which can bear one or more ketone functions; the ring members E, G,J, L and M, which may be identical or different, are chosen from acarbon, oxygen, sulphur and nitrogen; n is an integer ranging from 0 to4; m is an integer ranging from 0 to 5; the R radical, which may beidentical or different are chosen from a second Z group, which isidentical to or different from the first Z group, a halogen atom, ahydroxyl radical, a (C₁-C₆)alkyl radical, a (C₁-C₆)monohydroxyalkyl,radical, a (C₂-C₆)polyhydroxyalkyl radical, a nitro radical, a cyanoradical, a cyano(C₁-C₆)alkyl radical, a (C₁-C₆)alkoxy radical, atri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radical, an amido radical, a formylradical, a carboxyl radical, a (C₁-C₆)alkylcarbonyl radical, a thic)radical, a (C₁-C₆)thioalkyl radical, a (C₁-C₆)alkylthio radical, anamino radical, an amino radical protected with a (C₁-C₆)alkylcarbonyl,carbamyl or (C₁-C₆)alkylsulphonyl radical; a group NHRO or NROR″ inwhich RO and R″, which may be identical or different, are chosen from a(C₁-C₆)alkyl radical, a (C₁-C₆)monohydroxyalkyl radical and a(C₂-C₆)polyhydroxyalkyl radical; R₉ is chosen from a (C₁-C₆)alkylradical, a (C₁-C₆)monohydroxyalkyl radical, a (C₂-C₆)polyhydroxyalkylradical, a cyano(C₁-C₆)alkyl radical, atri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radical, a (C₁-C₆)alkoxy(C₁-C₆)alkylradical, a carbamyl-(C₁-C₆)alkyl radical, a(C₁-C₆)alkylcarboxy(C₁-C₆)-alkyl radical, a benzyl radical and a secondZ group, which is identical to or different from the first Z group; R₁₀,R₁₁ and R₁₂, which may be identical or different, are chosen from a(C₁-C₆)alkyl radical, a (C₁-C₆)monohydroxyalkyl radical, a(C₂-C₆)polyhydroxyalkyl radical, a (C₁-C₆)alkoxy(C₁-C₆)alkyl radical, acyano(C₁-C₆)alkyl radical, an aryl radical, a benzyl radical, a(C₁-C₆)amidoalkyl radical, a tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicaland a (C₁-C₆)aminoalkyl radical in which the amine is protected by a(C₁-C₆)alkylcarbonyl, carbamyl or (C₁-C₆)alkylsulphonyl radical; tho ofthe R₁₀, R₁₁and R₁₂ radicals may also together form, with the nitrogenatom to which they are attached, a carbonaceous saturated 5- or6remembered ring or which contains one or more hetero atoms, whereinsaid ring may be unsubstituted or substituted with a halogen atom, ahydroxyl radical, a (C₁-C₆)alkyl radical, a (C₁-C₆)monohydroxyalkylradical, a (C₂-C₆)polyhydroxyalkyl radical, a nitro radical, a cyanoradical, a cyano(C₁-C₆)alkyl radical, a (C₁-C₆)alkoxy radical, atri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radical, an amido radical, a formylradical, a carboxyl radical, a keto(C₁-C₆)alkyl radical, a thio radical,a (C₁-C₆)thioalkyl radical, a (C₁-C₆ )alkylthio radical, an aminoradical or an amino radical protected with a (C₁-C₆)alkylcarbonyl,carbamyl or (C₁-C₆)alkylsulphonyl radical; one of the R₁₀, R₁₁ and R₁₂radicals may also be chosen from a second Z group which is identical toor different from the first Z group; R₁₃ is chosen from a (C₁-C₆)alkylradical; a (C₁-C₆)monohydroxy-alkyl radical; a (C₂-C₆)polyhydroxyalkylradical; an aryl radical; a benzyl radical; a (C₁-C₆)aminoalkyl radical,a (C₁-C₆)aminoalkyl radical in which the amine is protected by a(C₁-C₆)alkylcarbonyl, carbamyl or (C₁-C₆)alkylsulphonyl radical; acarboxy(C₁-C₆)alkyl radical; a cyano(C₁-C₆)alkyl radical; acarbamyl(C₁-C₆)alkyl radical; a (C₁-C₆)trifluoroalkyl radical; atri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radical; a (C₁-C₆)sulphonamidoalkylradical; a (C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radical; a(C₁-C₆)alkylsulphinyl(C₁-C₆)alkyl radical; a(C₁-C₆)alkylsulphonyl(C₁-C₆)alkyl radical; a(C₁-C₆)alkylketo(C₁-C₆)alkyl radical; anN—(C₁-C₁)alkylcarbamyl(C₁-C₆)alkyl radical; and anN—(C₁-C₆)alkylsulphonamido(C₁-C₆)alkyl radical; a and y are integersequal to 0 or 1; with the following conditions: in the unsaturatedcationic groups of formula (II): when a=0, the linker arm D is attachedto the nitrogen atom, when a=1, the linker arm D is attached to one ofthe ring members E, G, J or L vertices, y can take the value 1 only: 1)when the ring members E, G, J and L simultaneously represent a carbonatom and when the R₉ radical is carried by the nitrogen atom of theunsaturated ring; or alternatively 2) when at least one of the ringmembers E, G, J and L represents a nitrogen atom to which the R₉ radicalis attached; in the unsaturated cationic groups of formula (III): whena=0, the linker arm D is attached to the nitrogen atom, when a=1, thelinker arm D is attached to one of the ring members E, G, J, L or M, ycan take the value 1 only when at least one of the ring members E, G, J,L and M represents a divalent atom and when the R₉ radical is carried bythe nitrogen atom of the unsaturated ring; in the Qationic groups offormula (IV): when a=0, then the linker arm D is attached to thenitrogen atom carrying the R₁₀ to R₁₂ radicals, when a=1, then two ofthe R₁₀ to R₁₂ radicals form, together with the nitrogen atom to whichthey are attached, a saturated 5- or 6-membered ring as defined above,and the linker arm D is carried by a carbon atom of the saturated ring;X⁻ is a monovalent or divalent anion; with the proviso that the numberof cationic Z groups in the compound of formula (I) is at least equal to1; and wherein said second compartment contains an oxidizingcomposition.
 35. The multi-compartment dyeing device according to claim34, wherein in at least one of said formulae (II), (III), and (IV), D isa linear or branched alkyl chain containing from 1 to 14 carbon atoms.36. The multi-compartment dyeing device according to claim 34, whereinin at least one of said formulae (II), (III), and (IV), D can beinterrupted by oxygen, sulphur, or nitrogen atoms.